7 Steps to Better Copy: How to Hire a Freelance Copywriter

Do you remember the last piece of writing that made you do something?

Maybe it was a bar’s chalkboard sign with an alcohol pun that made you stop in for a glass of wine. Maybe a sales rep sent you an email that resonated and made you schedule a demo. Perhaps you came across a big red sign with four white letters that made you stop.

Words are powerful. They communicate what a brand is about, what a service gives you and why you should do (or not do) something. Alongside serious leaps in technology, the power of words is only increasing.

That’s why the demand for copywriters remains high. Good content and clever writing is key for inbound marketing campaigns, viral social media ads, user-friendly apps and even print and broadcast advertising, especially in a noisy world where every app, device, screen and billboard is screaming for our attention.

Simply put: without good copy, your message is lost. Without a good copywriter, your message doesn’t have a chance.

Many companies don’t have the bandwidth for a full-time copywriter on staff, however, they recognize the importance of copy. There are email campaigns and print ads to write, mission statements to make and social media posts to craft. A company’s copy is how their consumers and investors perceive, digest and assess what they sell or provide. It makes sense to tap into the world of freelance copywriters for the flexibility and expertise they provide.

My earliest exposure to freelance copywriting didn’t involve me writing a word. In fact, I worked for the largest creative staffing agency in the US where I helped my clients hire the best and brightest creative freelancers out there. I had a behind-the-scenes look at the steps and processes companies went through to find the right talent and quickly learned what fostered a successful freelance experience versus a rocky one.

Now, as a freelance copywriter myself, I’m seeing a new angle of the business. Despite having a number of steady clients, there’s still a salesperson inside of me who enjoys hunting for new projects. That means I read far too many job postings looking for copywriters. It also means I read far too many job postings that will never get a second look from decent writers— and the person hiring for the project will, unfortunately, never know why they couldn’t find the right help.

With this unique perspective from both the client and freelancer side, I’ve assembled a guide for startups, companies and entrepreneurs who see the value of great copy— but need an honest inside look at how to get the expert they need.

Do your research

This is one of the most critical pieces of a successful freelance project. Start out by  understanding your project inside and out. Understand the goal of the project, the timeline in which you need it completed, any software or tools that might be necessary and investigate the typical rates of someone with this skillset.

The best projects I have worked on always began with a well-defined plan. When a client knows what they want, when they want it and are open to feedback and ideas to make the project better, that’s the holy grail of client and freelancer relationships. 

It’s worth visiting Reddit, UpWork and LinkedIn to investigate your project and the required skillsets. Ask questions, understand pricing and have a thorough understanding of what you want before you ever begin advertising the job.

Write a great job description

If you could build the perfect copywriter for you project, what would their portfolio, experience and style look like? The job description is your chance to attract and write to that exact person.

Importantly, this is also where you establish two important traits freelancers look for in a client: you know what you’re looking for and you’re enjoyable to work with. Your job description needs to describe and qualify while attracting talent. I disqualify projects that seem to be written without a plan or best intentions in mind.

Consider a few things:

• Do you need a topic expert or can a generalist writer take on the project? Consider your audience. If you’re writing an eBook for cryptocurrency experts, for example, you’ll want someone with extensive knowledge in the space.
• What are you looking for in a portfolio? Are you looking for someone who matches your existing copy, or someone who can shake up your style and tone? Can you identify a brand or campaign whose style you appreciate?
• Do you need someone who is senior or junior? Is this a project that requires serious research and an expert’s guidance, or can it be accomplished by someone who has a portfolio of good work and is merely taking direction?
• Do you need someone else in addition to a copywriter? I often bypass job postings that look for a developer/designer/copywriter because I don’t code or design. If your project reaches into areas of unrelated expertise, hire separate freelancers whose specialties can really shine.

• When do you need this finished? Find a due date and, for larger projects, set milestones to ensure the project is on track.

• What’s your budget? Some projects are paid hourly while others are a fixed project rate. If this is an ongoing project, like social media copy, an hourly rate can make sense as long as the freelancer knows the hourly limit. If this is a one-time project, a fixed budget may make sense. Be competitive in your pricing.

• Do you need this person on-site, or can they work remote? If they’re working remote, do they need to be located in a specific country or timezone?

Keep in mind that we may be reading a few dozen job postings each day. Write a concise job posting with keywords and deliverables clearly shown along with any software skills or writing experience you’ve deemed necessary.

A good job posting may look something like this:

Do you write for conversion? A SaaS startup is looking for an email funnel copywriter with private equity and finance experience for the following project:

• 8-10 sales emails for new prospects
• 3 subject lines per email
• Conversational, casual style
• Add emails to our Mailchimp account
• Make suggestions about how to best position our product benefits

This one-time project has a $300 budget and must be completed by July 12th following a 30 minute Skype call with the startup’s founder.

Please send your portfolio and relevant email funnel samples to us at email@email.com. We look forward to partnering with you!

It’s important to be complete and thorough with the job description, however, don’t fall into the trap of writing every detail of the project! Sure, you may prefer to collaborate in Google Docs and have twenty-seven content ideas, but the job description should be reserved for vital information.

Get the word out

Once you have a powerful job description, advertise your opportunity.

There are a number of popular resources for finding freelance copywriters, from UpWork to PeoplePerHour to Reddit groups. If you have a considerable budget, LinkedIn also offers job postings.

Additionally, there are staffing agencies and recruiters who can help you find talent, although usually at a premium price. The bonus? They’re often pre-vetted candidates who have a history with the agency so you know their track record.

Alternatively, social media is incredibly powerful for finding talent. A few months ago, I needed help from an SEO expert. After posting on LinkedIn and Twitter (using relevant hashtags), I had four introductions and two cold messages before the day was over.

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Review applications and conduct interviews

Assuming you’ve crafted a great job description and posted it to the types of places where freelance copywriters look for work, you have a pile of applications and a new question: how do I choose the right copywriter?

If you had a massive response, choice paralysis can be a real barrier to moving forward.

The way to go about choosing the right freelance copywriter? Deciding who isn’t right for the job.

You can generally disqualify candidates who:

Didn’t follow the directions of the job posting. If you asked for their portfolio and they’ve attached a PDF menu of their local Chinese restaurant, pass.

Have little to no relevant experience. A portfolio of children’s education print ad copy may be great for Disney, but it’s not right for your SEO blog post project on asbestos disposal.

Submit a budget that is much higher or lower than others. If they submit a low bid, they may not understand the full scope of the project or they’re simply not qualified or skilled enough to ask for higher rates and are competing on price alone. If they submit a high bid, they may be overestimating the project, are too senior — or you need to double-check your offered rate.

Don’t match your brand’s style or tone. Someone who has written dry but well-done content for a FinTech startup may not be right for a women’s yoga retreat. If you’re on the fence, ask for samples that they feel more closely fit the style and tone you’re looking for.

Don’t pass the social media investigation test. You may notice they appear to be more interested in Hemingway’s use of alcohol than his use of language.

Once you’ve narrowed it down to a few candidates, you can further define who is right for the project with an interview. Ask about their vision for the project, understand how many similar projects they’ve worked on and see if you’re able to attach any conversion stats or KPI’s to their past writing, if it’s relevant.

It’s not just about hard skills and writing ability. My favorite clients to work with are the ones who I enjoy speaking with and whose communication and feedback style best matches my own. When you speak with a freelancer, do they seem to match your style and personality? Do they respond in a reasonable timeframe to your emails or calls? Do they seem focused more on payment than on the success of the project?

Extending the offer

When you feel comfortable in choosing a freelancer, extend an offer with defined expectations. In writing, list the timeline, deliverables, your contact details and any information that sets a clear and established working relationship. Communicate how and when they’ll be paid.

Keep in mind that the best freelance copywriters are busy. Projects and opportunities can come our way at any moment so, if you’ve found a freelancer you love, move quickly. If you’re still on the fence, start with a small paid project to assess whether or not they’re right for a large project or continued work.

Getting started

If you do one thing after hiring a freelancer, do this: conduct an exploration call.

This is something I now insist upon before starting work. While it may seem inflexible, especially when there are deadlines, having a conversation about the project is vital. This is the time to brainstorm, suggest ideas and listen to their expert guidance on what to do to make the project a success. It’s the ideal moment to mention those twenty-seven content ideas you have, establish the voice and style you’re looking for and help the copywriter understand all that you know about the project, from your ideal customer to the path to purchase or even the idea behind the project.

Even after the exploration call, be available for questions. Copywriters who ask loads of questions aren’t clueless or ignorant, we simply need to understand the project and the details so we can deliver an awesome final product.

Working together on the project

While some clients are content to hand everything off to me and walk away, I enjoy creating a collaborative relationship throughout the project.

Give us your honest, constructive feedback when we submit work. Our first draft is unlikely to look like the final draft, so don’t worry if the first attempt needs editing. This is where your feedback is key. It’s impossible to get a great final result with vague feedback like “I don’t like it.”

Tell us specifically where you see room for improvement. If the tagline has a double-meaning in your industry that we may not be aware of, let us know that’s your concern. If you’ve tried similar messaging without results, tell us. Really, we can take the feedback.

At the same time, be open to pushback and guidance. While I’m happy to work with my clients’ expertise and guidance, I also understand best practices or techniques that they may not. It’s fair to ask for an explanation of our pushback— and I’m eager to explain my reasoning. Copywriting is collaborative.

An awesome partnership

One of the best parts of being a freelance copywriter is the ability to work with clients you love on projects you enjoy. I’m grateful for the relationships I’ve built with my clients and I’m convinced that every startup, business and entrepreneur has untapped potential simply by communicating more effectively with copy that has been crafted and obsessed over by a freelance copywriter.

Clients and copywriters have an important symbiotic relationship and, by making it easier to work together with these best practices, my hope is that we’ll all benefit through less frustration, more clarity and copy that inspires people to do.

For those who may hire copywriters, what questions do you still have?

Copywriters and other freelancers, what do you wish clients would do differently when working with you?

Image credit: Pexels.com

10 Sales Emails to Send When Your Prospect Goes MIA

“Sales emails to send when your client has been ‘on vacation’ for 4 months”

“Sales emails to send to prevent being fired”

“Meditation exercises for salespeople who cannot write an email that gets a reply”

“Convincing excuses to feed a sales manager”

If you’re in sales, you’ve probably Googled at least one of these phrases before.

Even after diligent phone calls and follow ups, carefully-written emails and a perfect demo, prospects can go MIA. They lose interest, buy from a competitor or simply wander off into the woods and start a new life as a reclusive outdoorsman.

And, if you’re like me, there’s nothing worse than a prospect who goes MIA.

Even a “no” is preferable to silence. At least it’s feedback. Early in my sales career, it seemed as if many prospects I spoke to found themselves wandering into the Vermont wilderness, never to be heard from again.

Fortunately, I eventually did learn how to write sales emails that get responses and continue to do so for a number of clients including tech startups, staffing agencies, design boutiques and for my own client growth.

Some of the strategies I’ve found to work are obvious. Many aren’t.

But if the quarter or month feels like it’s constricting around you like a python and you need to start getting answers and moving prospective clients down the funnel, you can bet you’ll start getting responses from at least one of these tried and true email strategies.

It’s Not About You
There are a few dozen sales email templates that circulate most sales departments. If we step back and look at them objectively, they’re usually almost entirely about us, the salesperson, and what we want from a client.

We want their time. We want their attention. We want their money. We want their signature.

And, if we’re capable salespeople, we should ask ourselves in each email we write: what’s in it for my customer? What do they get out of this?

Even an email in which all you need to do is get their signature to start their service, which on  the surface benefits us most, we can spin it to be about them. Instead of asking for their signature, we have to explain why it matters to them. Perhaps, if we get their signature today, you can prioritize their onboarding or lock in the special offer that ends this week. What’s in it for them?

Get a Response
Let’s assume you sell a SaaS product for a startup. You had a demo, the client seemed interested, expressed their desire to hear more, has a quote— and then your prospect went MIA and disappeared.

They’re not opening your old emails. Their voicemail is full. The month is ending soon. You think you’ve tried everything short of coming to their home with a pen and contract.

So, how do you get a response? Try (at least) one of these 10 sales email strategies.

Add Serious value
When I worked for a SaaS company that served small retail businesses, I’d make sure my prospects knew I understood their industry. One way to prove credibility and catch them off guard with a follow up that none of your competitors use?

Add value.

If I hadn’t heard from a prospect in some time, I would check their company social media accounts and let them know about a tool I’d learned about could help them attract more followers. I’d direct them to an article about new trends for stores just like theirs.  

Of course I’d include a subtle call to action in the email, but 97% of the content would be beneficial to them. If what you sell can be hard to distinguish from its competitors or you’re selling in a crowded space, being the most helpful and valuable salesperson your prospects work with can be one of your greatest strengths and this email creates that perception.

Make an Intro
Using a similar mentality to the value add email, making an introduction to your prospect can create serious goodwill.

If I’d spoken with a client who mentioned customer loyalty was important to them, I’d introduce them to a partner who could provide an integrated loyalty program. If they needed branding, I introduced them to a graphic designer. If they wanted marketing help, I introduced them to an agency.

Tread lightly with this one. Your prospect may not want to be introduced to anyone and, if you get the sense they’re quite private, this email can simply be used to ask if they’d like an introduction. I usually took the initiative and made the introduction proactively, but use your discretion.

Whichever method you choose, it shows you’re serious about their success and want them to do well. You’ve gone from just another salesperson to someone they can rely on, a trusted partner.

What’s helpful?
Even if you’ve asked about next steps at the end of each call, prospects and salespeople can lose touch with what needs to happen next. Maybe the prospect changed their mind or something unforeseen happened on their end.

I found it worthwhile to ask them: what would be helpful to you? It might read like this:

(Prospect Name),

We loved having you on the demo last Wednesday! It sounds like we’re a great fit for (Company Name)’s desire to (something they want to do) and I understood that we were to connect this week to figure out what happens next.

I’m curious: what would be helpful to you at the moment?

If you’d like to schedule another demo, speak with a partner or get on a phone call, please let me know how I can be most helpful to you.

This email lets you ask about next steps in a way that a prospect perceives as helpful and customer-centric, not intrusive.

Multiple Choice Answer
If a prospect has been silent for quite some time, this style of email allows you to interject humor into the conversation while figuring out next steps.

With bullet points listing a specific possibility, tailor it to your last conversation and ask them to choose which situation best fits their current position. It may look something like:

Last we spoke, you mentioned you still had construction at the store and it may delay your decision. Which of the following best fits where you’re at now?

  • I’m ready to go, just give me a call!
  • This is delayed a few weeks, but I’m definitely interested.
  • I need something else from you like a demo, additional quote or a phone call.
  • I’ve chosen to go a different route and am no longer interested.
  • The construction project’s excavation opened up an Indian Jones-style archaeological site and we’re just waiting on Harrison Ford to get here— but I’m still interested!

Tailor the humor to the person you’re speaking with. Write something you suspect they’ll resonate with.

Step-by-Step Email
I was amazed to learn how big of a barrier not understanding the steps of the buying process could be to buyers, especially outside of enterprise sales.

Sometimes all it took to close a sale was to break down what happens next.

If you think your customer may be unclear as to what happens next, send them an email that outlines in 3 brief, short steps what needs to happen to become a customer. It could look like this:

  • After a quick demo, we find which package works best for you and decide upon an annual or monthly plan, based on your budget.
  • With a signed agreement, we’ll take payment which can be offered on 60 day terms.
  • You’ll work directly with our customer success team and experience unlimited training and 24/7 support whenever you need it!

Make sure the steps are simple and concise. Be specific if you can directly address a concern or detail related to this customer.

Social Proof Email
Do you eat at a restaurant on Yelp with 2 stars? Do you cancel your Uber trip when the driver is shown to have 1 star?

Social proof matters and we do make decisions based on others’ opinions and feedback.

This strategy walks the line between self-interest and self-promotion and being helpful to your client. It’s what I call the social proof email and it may read something like:

Hey (Client),

I just spoke with Jim who joined us in May as a client. He said the integration with WordPress has been perfect and he’s even been able to do (two things the customer was interested in).

This was a major concern of yours and I’m glad to hear it can be resolved easily. When could we set up a brief phone call about getting started with (Company)?

Bonus points if you have a client who loves you so much they’re willing to speak directly to your prospects as a brand advocate, an introduction you can make in a separate email.

Super Short
Most likely your prospect is busy and reading emails on mobile.

You don’t have much time to get their attention.

Experiment with short emails and show them you value their time:

(Prospect Name),

You mentioned a loyalty integration is vital for (Business Name).

Here’s our fantastic partner who can do exactly what you’re looking for.

Knowing they’re a trusted option, does this allow us to work together?

GIF Gold
I’m a believer that GIFs shouldn’t be relegated to Twitter. Whether you call them “GIFs” or “JIFs”, visit giphy.com and see what you can find that will help spark a new conversation.

I had a client who’d gone MIA for weeks. She mentioned their printer, which was central to their business, was no longer working. I sent her the following:

(First Name),

Last we spoke, your printer was keeping you from continuing a conversation about (product).

Did you get it solved, or have you taken a more creative approach?

(For anyone who didn’t click the link, it’s a GIF from the movie Office Space where they destroy their long-hated printer with baseball bats and serious enthusiasm.)

I had a response within minutes.

The Compassionate Salesperson
Salespeople aren’t always thought of as human-beings. Our prospects usually know what we want. They’ve heard the jokes and seen the movies about sales people.

So, what happens when you break that stereotype?

If you’re in sales, you probably/hopefully have a great deal of empathy. I often connected with my clients and genuinely cared about their success, so when they went MIA it was a bit like being ghosted by a friend.

Borrowed from a previous sales team, this email worked wonders in finding out where they went:

Subject Line: Are you ok?

(Prospect Name),

We’ve had some great conversations and, last I knew, you were interested in getting started with (Product).

However, I haven’t heard from you in a while and that’s unlike our previous communication.

Is everything ok?

This suggestion might sound incredibly manipulative. In some sense it is. But it’s also valid in that I had several clients or their business partners respond to tell me they were, in fact, sick and in the hospital or had suffered some major setback.

One prospect even died, however, I’m confident our service wouldn’t have prevented it.

This not only lets you put some empathy and concern for others out into the world, but it also helps you understand what’s happening in the personal lives of your prospects.

We’re Breaking Up
If you’ve tried many phone calls over the course of many months, sent creative emails, schemed with your sales manager on a way to get their attention and there’s still no response, it’s time for a new plan: the breakup.

Breaking up can be hard to do with a prospect, especially if you’ve spent a great deal of time with them on calls or demos. However, at this point, they know you’re available and ready to take their call, the catch 22 of being skilled at follow up. They have the upper hand and know you’ll come running back when they want you.

Create scarcity and see what happens.

By sending emails that announce you’re going to stop reaching out, you create a sense that you’re going away. They need to do something to prevent it— and the best way to prevent your sudden scarcity? A response.

It’s helpful to send at least one breakup email. In each one, I ask a variety of questions: what would be helpful, what have they chosen to do, when might be a better time to discuss their needs? You can also drop in helpful links to add value, like a webinar or article they’d find useful, plus a link to Calendly so they can set up an appointment in 2 days or 2 years.

Another strategy? Ask for feedback on your sales style in the final, final email. I’ve sent an email similar to:

Subject: Was it me?

(First Name),

I’ve enjoyed exploring (Product) with you, however, I haven’t been able reach you.

Perhaps you’ve chosen to go another direction, but I’m always looking for feedback from those I enjoy speaking with: what could I have improved or done differently that might have let us work together?

Hope you’re well!

I’ve received helpful feedback. I’ve been told I was too aggressive. I’ve been told I was the better salesperson among my competitors, but it came down to features we didn’t have.

The breakup emails can be the final push that gets them back in touch, thanks to scarcity.

If You Want to Sell, Don’t Do This
There’s plenty of great sales and writing advice out there. There’s just as much, if not more, terrible sales and writing advice out there.

These strategies live firmly in a category I call: “Please, just don’t.” I see some of these ideas suggested in “how-to write a sales email” articles and can only hope salespeople aren’t using them.

  • “My manager asked me to follow up.” It’s one part used-car-negotiation-tactic corny and one part I-must-be-working-with-the-worst-rep-in-the-company concerning.
  • “My manager asked me to close your file.” Does your prospect care about your Salesforce pipeline? Nope.
  • “Hello Sir/Madam…” It takes seconds to personalize an email to your prospect who you’re asking to spend hundreds or thousands of dollars and potentially hours of their time to implement your solution. Look at your notes, find out who they are, what your last conversation included and what their unique motivations are.
  • “Dear Sir, We request that…” Victorian English sounds great when you’re reading Charles Dickens, but overly formal language loses everyone. I have yet to meet a CEO or senior decision maker who speaks like Frasier Crane. I use my Midwest, casual tone like I’m speaking to a neighbor or friend.
  • Writing War and Peace This isn’t the place to write 1,700 words. It’s a place to write few words and communicate your ideas succinctly. If you need to explain something complex, try hyperlinking the text to a video, article or infographic that can more completely communicate your thoughts— or communicate via phone.
  • Not using “because” The word “because” will become your best friend because research has shown it leads people to comply with what you’re asking— even if it’s a terrible reason. “Hey, can I borrow your car?” is, according to research, weaker than “Hey, can I borrow your car because I’m competing in a demolition derby on Tuesday.”I’d recommend making whatever follows “because” as compelling as possible, however.

A Few Final Thoughts on Sales Emails
Even with inbound marketing becoming more and more common in companies, being an effective email and outbound sales-style writer will help prevent your prospects from going MIA and killing your quota and quarter.

But it’s not always easy to figure out what works. For some industries and clients, these email strategies will be a slam dunk. For others, there will be crickets until they’re polished to speak to the prospects’ interests and style.

That’s why it’s important to craft tailored sales copy, targeted for your clients, unique selling points and tone.

If you’re looking for sales emails and messaging that speaks powerfully to your prospects, that’s where I come in. I work consultatively and collaboratively with my clients, using what I learned from my sales career in staffing and tech sales, plus continued feedback from my current clients.

Let’s work together to ensure you have your best sales month, quarter and year yet.

Photo by Tim Gouw from Pexels

Confessions of a Gary Vee 2017 Flip Challenge Dropout

I started 2017 so well when it came to hustling.

I’d work my tech sales job during the day, then spend the evening on LetGo, OfferUp, Craiglist and eBay, buying and selling, with every intention of hitting Gary Vee’s $20,017 flip goal.

I did well for the first few weeks, diligently tracking my profits, margins and inventory. At some points, I was on track to hit the lofty $20k goal and earn significant income. I wrote blog posts about the Flip Challenge, recorded videos at junkyards, interacted with other flippers on Twitter and took dozens of trips to the local post office to ship out sold products.

I might have singlehandedly influenced the stock prices of shipping tape manufacturers.

But life happens. In May I sold my car, quit my job, donated many of my possessions and packed a few bags (plus a mountain bike) and moved to Montenegro to live with my longterm girlfriend.

(This was a decision with much more consideration than the previous paragraph might indicate.)

I spent the next couple months adjusting to life as a full-time freelancer, navigating a new culture and language, plus exploring new parts of Europe. I deleted OfferUp and LetGo apps from my phone. My meticulous sales spreadsheet sat unused as a Google Sheet. My frequent eBay sales stopped.

Montenegro doesn’t have the same opportunity for flipping like the US does. For one, my Montenegrin is lacking to do any serious negotiation in buying or selling. And, even if I could buy and sell, shipping anything out of the country is expensive and would eat my profit. I gained a new respect for many of the European flippers who I’d seen struggling through the Flip Challenge due to shipping costs and geographical limitations.

Initially, I felt a little guilty about dropping out. I’d seen the earning potential and enjoyed reinvesting my earnings into new items. I liked seeing updates from others who were discovering their potential, both financially and personally. Gary’s encouragement of getting off the couch and using your free time to make serious money and gaining skills resonated— but it simply didn’t make business sense once I was across the pond.

Short-lived guilt

These feelings of guilt didn’t last long.

Since I was 15 years old, I’d worked for someone else. I’d always flirted with self-employment and side hustles. I’d detail cars, sell car parts and modify watches, but at the end of the day my living came through a paycheck signed by someone else. It was clear to me, however, that I was my happiest and most energetic when working for myself or a few clients I enjoyed partnering with.

Moving to Montenegro meant I couldn’t flip, but it pushed me to finally pursue self-employment through freelancing. For the first time I got to choose what I did each day. After working in sales where I’d become used to a work-or-starve mentality, freelancing wasn’t a difficult transition and I attacked the freelance market with the same business development mentality I’d built over the past few years.

My career transitioned, almost by accident, to becoming a copywriter. I expanded my marketing knowledge and skills and offered sales consulting for startups who need sales guidance.

The Flip Challenge’s Effects

Importantly (and quite serendipitously) the 2017 Flip Challenge came to me at a critical time in my life. More than the income, I gained realizations more valuable than the financial profit.

The Flip Challenge showed me the value of hustling once again, something I’d nearly forgotten after working for others.

The Flip Challenge let me take small risks and build up a feeling of confidence in my abilities.

The Flip Challenge showed the value of good content and marketing and the power of social media as Instagram became a great platform for selling.

The Flip Challenge helped cement some basic business accounting and business math skills into my repertoire.

The Flip Challenge exposed me to manageable failures that made larger failures much less intimidating.

The Flip Challenge underscored the idea that making money isn’t necessarily glamorous or easy— but a lot of fun.

The Flip Challenge helped me set a dollar value on my time, something critical for freelancing, to determine whether or not a sale was worthwhile or not.

The Flip Challenge awakened what it’s like to work for the love of what you do and that it’s possible to stay up until 2AM absolutely buzzing, loving your work.


To others still flipping

From a few searches on Twitter, the Gary Vee 2017 Flip Challenge is still roaring along for many people— and some are even brave enough to jump in 10 months into 2017.

If you’re still flipping, keep up the hustle. But whether you hit that goal or not, focus on what else this challenge gave you. You might be surprised to see how much your mentality, appetite for risk and business skills have grown since you first started.

Whether you end up making $20.17 in profit or $200,017 in profit, the value of the growth possible from this challenge far outweighs the monetary benefit.

And, for that, I’m grateful for Gary Vaynerchuk’s challenge.


3 Sales Tips for Startups That Don’t Print Money

Unless your startup is in the business of printing untraceable, impeccable counterfeit currency in large bills, you’ve got to make sales.

Assuming you’re not in a business that puts you on an FBI watch list, making a sale could be the difference between getting funding, growing your team and making it to IPO– or packing up your office and crawling back to the 9-6 cubicle job you escaped.

Not every startup founder has a sales background or, if they do, they may not have the time to properly focus their efforts on sales. It doesn’t matter if you’re a developer who has never sold a thing in their life or a seasoned sales veteran who is negotiating a lease, hiring a team, polishing a product and finalizing branding, sales doesn’t always rank high on the to-do list.

Granted I’m a sales guy and not a CPA, but I’d venture this is a really, really awful way to go about paying bills. Until landlords begin accepting promises of a great user experience on the mobile version as a form of rent payment, you have to sell.

Whether you desperately need to make your first sale to stay afloat or you’d like to walk into your next investor meeting with even better results than promised, these are tested ways to start making sales soon.

(I know because I tested them.)

Upsell your current clients (if you have them)

This is either incredibly obvious or it’s so obvious that you might’ve missed it– but there’s much to be unpacked here.

Arguably the best place to start increasing revenue is with the people who’ve bought from you already. They know about you, you have an agreement or their credit card on file and, ideally, they like you. You won’t need to spend much in the way of marketing dollars– and they’ll convert at a much higher rate than new leads.

Upselling your current clients can feel uncomfortable until you’ve had experience doing it. It’s a feeling of: really, these people who have been paying me– I’m going to go back to them and ask for more?

Yes. Yes, you are.

For one, if they’re your customers you’re bringing them value. And if you have the opportunity to give them a new tool, feature or offer– don’t they deserve to know about it? What if it transforms their business? Do you know your client so well that you can make the decision for them that they don’t want to buy more from you?

Imagine if your favorite app fixed one tiny feature you’ve always been bothered by with a $5 premium version– and you never found out about it because they didn’t bother to send out an email or announce it on social media.

Frustrating, right?

What does it look like when we talk about “upselling” your current clients? Here are a few areas to focus on:

Look at your agreements. Could you offer your client a slight discount if they’re willing to prepay for their next six months of service or sign an annual contract? Put yourself in their shoes and think of compelling reasons for them to sign up for more of your service, for longer and, ideally, with a chunk of cash up front for liquidity. This means the money will continue to roll in– and you spend less time worrying about churn and having to find new clients.

Look at your client relationships. Do you feel comfortable asking your clients for referrals? Referrals are testimonials and lead gen all in one– and four-times more likely to lead to a sale. I was consistently surprised how willing my clients were to offer up referrals or introductions when asked.

Look at your products and services. Is there room for a premium version, some way to white label and resell a related product– or is there a gap in your offerings that you can fill? What has your sales team been hearing from your clients that seems to be missing or lacking– and can you solve this in a way that has great ROI?

Look at your sales team’s commission plan. Are your sales people rewarded and motivated to not just maintain current clients, but grow their accounts? Do you take into account the fact that it’s more expensive to get new clients than maintain existing ones– and incentivize based on that fact? Is it possible to hire a salesperson whose sole job is selling to existing clients?

One important note: this really only works for happy, content clients. Know when to upsell and when not to. Build a sales team around great client service and a product team that takes feedback from your clients.

And to those of you who can only wish they had existing clients, just keep this strategy in your back pocket when you do have clients to upsell. It’ll happen.

Partner up

Hands down, this was one of the most powerful strategies I employed while working at my first startup for new business– and it’s one that many companies use to make sales.

The goal? Find partners who can introduce you to new business.

When approaching a possible partnership, your messaging needs to show that this is a mutually beneficial relationship. Maybe after some discussion about what’s important to them, you’ll offer commission or a spiff on every client they introduce you to.

Either A) they’re going to make money off of you through commission, sales or residuals or B) you’ll add value to their clients so they’ll introduce you for free.

How can you identify lucrative partnerships? Start here.

Consider your product. Is your product easily integrated with a major platform like Shopify or Salesforce? There are entire channel and partnership teams who would love to know about what you do so they can expand their product ecosystem.

Consider your market. Are there similar businesses in your industry that aren’t direct competitors– but serve the same type of customers? Send them an email and find out what they look for in a partnership and start referring business to each other.

Consider consultants and agencies. Marketing agencies and consultants make a living introducing their clients to new products and services to help them solve problems. If you sell an eCommerce plugin, wouldn’t it make sense to partner with a digital agency so they can add your tool to every site they sell?

The great thing about agencies (and why I always targeted them) is that they usually have a handful of clients– and are looking to bring on others. If you sign one agency, you now have access to multiple clients– instead of chasing after one single client.

Consider white labeling: If you don’t mind someone else taking credit for your product while you count the cash, this can be a smart option. Your branding is scrubbed from the product and replaced with the partner’s branding or interface– but they sell it.

This is especially helpful if you have a small sales team or haven’t sold before. Let someone else do the selling!

The big benefit of partnering up? You can work with dozens of partners who will feed you leads and clients. Instead of having to chase 50 cold leads, you’ll have partners who are equally invested in making a deal happen– and you’ll come recommended.

Find a company’s partnership or channel sales team or, if they’re quite small, someone in marketing, product or sales. They’ll typically be your best chance at getting a reply.

I’ve been on both sides of the partnership coin, from creating partnerships to getting paid commission from one. They were my highest value business relationships.

Revisit old leads

It’s what every salesperson doesn’t want to be asked to do by their manager.

I’d always think: really, I’m going to call someone who’d previously told us ‘no’?

And then I’d close a sale using that strategy and realized that’s why sales managers tell their teams to comb Salesforce and find old leads. I began hitting old leads and found thousands of dollars worth of sales.

I’m a big believer in disqualifying leads that will obviously waste your time so be ready to move on from them if it’s clear there’s no potential. However, you might be shocked how much cash is sitting in your CRM.

Think about it:

• This director might’ve been called around the holidays. Between Christmas shopping and family travel, they didn’t have the time to even think about your product. Now it’s January and they want to hear more.

• The person who’d told you “no” before doesn’t work there anymore; they were fired for making awful decisions, like not investing in awesome products like the one you’ve built.

• They’d used all of their budget and couldn’t make a deal happen, but it’s a new fiscal year– and the money is back and they’re ready to buy!

• The payment terms you were offering didn’t make sense for them– but your finance team now lets clients break up payments in quarterly chunks and it becomes possible for your client to buy.

• The integration they needed that you didn’t have before was just approved as a beta version– and it’s time to let your new client know the one road block that prevented you from working together has been cleared.

• They bought from your competitor and your competitor absolutely sucked. The onboarding didn’t go well, they’ve had four account managers in three months and it’s not working how they were told it would.

• The last sales rep they spoke with from your team? They didn’t click. There was nothing about the pricing or product they didn’t like, but the last guy’s used car salesman style turned them off.

Literally every single one of those scenarios has happened to me.

If you’re using some sort of CRM or even just a spreadsheet to track leads, also track why you’ve “lost” the sale. Over time this will help you identify common traits in leads that don’t close, shortcomings in the product, issues with pricing or even common objections to train on further.

A bonus tip

Over the years, I’ve found that sales is a science: you introduce new variables, attempt to add in as many controls as possible and test new hypotheses. Sometimes you’ll find a theory that works for a month– and then never works again. The Invisible Hand or some unknown force changes everything, I suppose. But what’s important is that you try something for a while to give it time to mature and find out if it’s effective.

No, you don’t want to have a losing strategy for a year– but don’t change course on a daily or weekly basis. Build a strategy that you try on a few leads or clients, change messaging, test new call approaches on low-quality leads to see how they react. But overall remain consistent with the same amount of activity, similar methods and approaches. You’ll eventually get a feel for what’s working.

Sales is far from just picking up the phone, making a few calls, being polite and slick with words. It’s a daily effort of keeping positive and motivated, being consistent, having high emotional intelligence and knowing how to move a conversation from “I’m not interested” to “How do we get started?”.

If you’re new to selling in a startup environment, the good news is you have all the agility and flexibility you could want. Focus on what works, take care of your clients, add value to every interaction and be the most useful person they’re speaking with that day.

Or at least until you can figure out a way to be the Uber of counterfeiting.

Photo Credit: Viktor Hanacek

Sell Booze at the Beach– And Other Lessons I Learned While Working With 200+ Small Businesses

If you’re looking for almost certain small business success, open a liquor store near a beach.

That’s one small business lesson.

But if you’re reading this, especially if you’re not looking to sell cheap vodka to college kids on spring break, you’re more likely hoping to find out what practical and actionable lessons could help you.

As part of the sales team for a tech company, I worked with over 200 small businesses across the Midwest and East Coast, from established bike shops to brand new clothing boutiques to the aforementioned beachfront liquor stores.

Especially from the viewpoint of a salesperson, there’s a misconception that sales is all fast-talking, clever pitches and hard closes a la Glengarry Glen Ross. In reality, the closers getting the coffee in 2017 do much more listening than talking.

With all that listening over the course of thousands of phone calls and demos, I began picking up on trends. I began to see patterns in the businesses that called to cancel service after closing within three months– and those that called to add more locations to their account as they expanded.

While geography, demographics, market demand, business plans and previous experience will dictate a great deal about the success (or failure) of a small business, there are undeniable do’s and don’ts that separate those closing their doors and those opening new stores.

Here are the lessons I learned from the best business owners– and their out-of-business competitors:

They build relationships, not transactions

This is a lesson I’d learned early in life watching small businesses I worked for “nickel and dime” their customers to death. The owners were so focused on margins on each sale that they neglected to consider the impact on the experience and lifetime value of a customer. There were no extras or freebies, every moment was monetized and short-term profit came way before customer satisfaction. Sales became transactional and impersonal.

As a certain fascist chef might say: “No soup for you.”

The best clients I worked with saw the value of a happy customer– and not just a margin. Bike shops would offer free clinics and flat repairs. Clothing boutiques employed a “personal stylist”. Employees knew customers’ names, their preferences and created an experience during their visit.

It’s a race to the bottom if you’re competing only on price, location or selection. Great service that leads to relationships will have your customers driving past your more convenient, better stocked and cheaper competitors– and telling their friends about you.

Another big benefit? You’ll better understand what your ideal customer profile is and this will help decide everything from pricing to marketing to in-store experiences and promotions.

You can’t effectively sell your service or product without really understanding who needs it.

They reward customer loyalty

Customer loyalty, especially as a result of fantastic relationships, is key. For one, some estimates show that acquiring a new customer is six to seven times more expensive than keeping your current customers happy.

Loyalty programs like Thirdshelf are a fantastic tool for rewarding your customers for their continued business and support– as a supplement to offering great customer experiences. The more they shop, the more it pays off– for both them and the business. In fact, 69% of consumers say they choose where to shop based on where they can earn points or perks– meaning if you’re not even offering a loyalty program, the cards are stacked against you.

For small businesses that are worried only about the short-term, they’ll see a rewards program as a loss, product going out the door without generating maximum revenue. The savvy clients I worked with knew that a well-considered loyalty program and its perks were a guaranteed way to keep customers coming back and buying more.

It’s not enough to just throw an offer at your customers. Pay attention to what they buy and what promotions draw sales. Yes, your loyalty perk is great for the customer, but make it work for you, too.

They get over sunk costs

If you’re not familiar with a sunk cost, Merriam-Webster defines it as “a cost already incurred that is not subject to variation or revision…”

To give you an example, the business cards you purchased where your last name has a typo? That’s a sunk cost. You’ve already paid for the cards. They can’t be fixed. And, unless you’re someone really special, your misspelled business cards don’t have any resale value. Go ahead and get new ones printed.

Unfortunately, I came across this mindset quite often with small business owners. They’d invest five-hundred dollars in a poorly built, buggy eCommerce website their high-school nephew built. Even if it didn’t function and was literally costing them money through lost sales, they couldn’t imagine scrapping the whole site and starting over– even if a new solution would solve all their issues.

The successful businesses I worked with made smart, well-researched decisions and certainly weren’t careless with their money. But if they saw a tool, platform or solution that would make a difference, they were willing to abandon their old ways. Their eyes weren’t focused on buyer’s remorse but on what would make their business profitable.

It’s never fun to realize you wasted money on a bad decision, but if there’s no possible way to benefit or recoup the investment, it’s best to move forward and find what does work. You won’t ever benefit from protecting yourself from the realization of a bad choice or wasted money– and you’re only compounding your mistake by not moving on quickly.

They use technology to their benefit

kaboompics_Young Entrepreneur Working from a Modern Cafe

Photo Credit: Kaboom Pics

While selling a tech product I recognized quickly how resistant to technology many business owners are. They had tools one Google search away that would give them more data than they’d ever had, free platforms that would manage tasks they were paying people overtime to manage and incredible ways to market and advertise their business for a few bucks.

Coming at this as a Millenial I’m biased; I remember VHS tapes and “car phones”, but most of my life I’ve had access to the Internet. The point still stands, however. The technology that offers the most utility and function wins out.

It’s no different for small businesses. Software isn’t just for enterprise-level companies with huge IT teams and budgets. There’s a thriving marketplace for small-business technology that doesn’t require a PhD in Computer Science. Most offer awesome support and easy-to-use interfaces.

Just about anyone can build a Shopify or WordPress site to have an online presence– and if you’re not online, your customers aren’t finding you. A point of sale like LightSpeed can help you manage inventory, customer data, sales history and reporting for relatively little money. UpWork can help you hire freelancers from all over the world to rewrite your sales collateral or design a new logo. Marketing on Facebook, Instagram and Twitter using tools like Buffer or HootSuite are unbelievably more cost-effective than print ads, flyers or billboards. Many businesses make the bulk of their income by selling through Amazon or eBay.

Technology has been democratized. It’s within reach for those who are willing to look for it and spend some time evaluating what they need and what solutions exist. My A-team clients embraced technology– from how they hired to how they sold to how they ordered product to how they reported their accounting.

And if this still sounds outside of your comfort zone, there are plenty of consultants and agencies out there who can help you with your technology, marketing and operations. Specialization and focusing on what you’re best at has its benefits.

They make it easy to buy


Photo Credit: Mike Petrucci

Perhaps loosely related to my last point about embracing technology, smart business owners make it easy to purchase from them.

It starts with being found in the first place. Again, good businesses are not relying on placing flyers under windshield wipers in local parking lots– and they aren’t just hoping someone walks into their business by chance. They’re marketing online, they’re growing an Instagram and Facebook following– and closely monitoring those channels for customer feedback. They have an active Yelp presence and watch Google for reviews. They have a well-built and thoughtfully designed website that shows what their products and services are, how to contact them and links to social media accounts, customer testimonials and more.

My recommendation: ditch the inflatable purple gorilla advertising your 10% off sale and use marketing tactics that really work.

Once you have your a potential customer’s attention, converting them from potential to paying is vital. If they’ve come this far, you don’t want to lose them now– especially if you’ve invested a few marketing dollars into their interest.

Should they find your site and want to order online, your purchase process should be straightforward and logical; don’t make them go through fifteen mandatory forms and only accept one obscure payment type. You should have a quick check out process and accept all major credit cards and PayPal.

Should they find you in real life or walk into your retail store, their buying experience must be similarly simple and easy. Your store layout should be logical. You should pair related products together. You should know exactly how many of each item you have in stock. You should know what services people want. If you schedule appointments, make it so people never have to call in with a tool like Booxi— because, most likely, they’ll avoid the phone.

When it comes time to buy, checkout should be easy. Accept credit cards– and accept the fact you’ll be paying a processor a fee to do so. You’re better off paying the fee than losing this customer’s first sale– and future second, third and fourth sales.

You should be capturing their information (name and email, at minimum) which makes it easier to see what they bought in the past, handle returns or exchanges and create a personal touch. Tied into an intelligent marketing plan, this is one of the most valuable points in the entire sales process.

Ideally, you’ll embrace an omnichannel solution where your inventory, customer data and shopping experiences are shared across online and in-person platforms. Customers can look up the shirt they bought online so they can buy the same shirt in a different color when they’re in the store. They’ll be able to see how many reward points they’ve earned by shopping online and in your store– all from their iPad at home. Your inventory will update across channels so you’re never selling products in-store or online that don’t exist.

This really amazing idea isn’t reserved for only mega-businesses; there are plenty of small business solutions that offer this for a few hundred bucks a month and can connect with a number of eCommerce and point of sale technologies.

Here’s the good news

If you watch the news or read the newspaper for even five minutes per year, you’ll see the doom and gloom around retailers and small businesses. Macy’s is shutting down nearly 70 stores in 2017 while Amazon buys out Whole Foods; the ground is shifting. The business landscape is changing, but that will be great news for nimble, intelligent small businesses who embrace their customers, use technology and remove barriers that kept customers from buying.

Unlike a business like Macy’s which would take six months, ten McKinsey experts, fourteen departments and forty-six meetings to make small changes, a small business can make major changes quickly and easily.

Small business is the speedboat to Macy’s Royal Caribbean cruise ship.

My recommendation? Examine your business from top to bottom.

Imagine you’re about to appear on Shark Tank and Mark Cuban will grill you on how much you pay for your products, what you’re doing to attract new business and what your unique selling points are– just before Robert Herjavec jumps in to ask how you gauge customer satisfaction.

How would you do in answering their challenges?

Look at your entire business. What’s working and what isn’t? What have you been putting off and know you need to finally tackle? What’s the best part of your website (and is there a best part of your website)? How do customers find you? What product or service do you make the most money on and how might you get more people to buy it? What do you hear from your customers– and do the one-star reviews on Yelp hold any truth to them?

There’s a great deal of low-hanging fruit and new customers to go after right now if haven’t explored new strategies and technologies for a couple years. But if you’re not entirely sure where that fruit is hanging, how to get those new customers or how to really consider your options, I can help.

If you’re part of a small business or startup and you’re ready to begin making those changes, I work with businesses just like yours. From social media strategy to identifying tech tools that fix problems and more, I always start with a discovery call to understand more about your business including its challenges, opportunities and goals. 

Let’s put 20 minutes on our calendars and get these improvements started. You’ll be glad you did.

Featured Image: Alex Iby

Staying Positive During a Job Search: A How-To Guide

Nobody really wants to look for a new job.

It’s usually something we have to do– like sitting through commercials on Hulu or accepting your coworkers friend request on Facebook– even if it means employment, more money or a work/life balance.

It falls into that uncomfortable Bermuda-triangle-like zone of financial stress, uncertainty and rejection. Add in some hurt pride if the job change wasn’t exactly your idea.

Unless you’re the type of adrenaline and risk junkie who finds joy in feelings that we’re probably evolutionarily predisposed to avoid, these aren’t emotions or experiences you’re particularly excited about having.

If you’re in the middle of a job search right now you know exactly what I mean.

But it happens. You want to leave a job or the job wants to leave you. If trends continue, job changes will be as common as watching the Olympics every few years. According to PwC, 25% of Millenials expect to have six or more employers over their lifetime.

So this job change thing? It’s likely to happen more often– which could be great news.

The more we do something, the less scary it is each time– and the better we are at preparing for it, moving through it and thriving. I’m a big believer that happiness is correlated with expectations, so if we expect to change jobs frequently and experience volatility, our happiness won’t take the beating it would otherwise.

But it’s easy to rationalize through it when job hunting is an abstract concept. A job search, whether you’re still employed or not, is stressful and it’s easy to feel defeated and pessimistic.

I’ve searched for work a number of times– sometimes with a job and sometimes without– and worked for four years in sales positions. It’s the time I spent in sales that helped me build a toolkit for staying positive and it can be directly applicable to a job hunt as well. Rejection, financial pressure and uncertainty live in both sales and job hunting– but the good news is there are solutions that work.

Here are a few ways you can stay positive– even during the toughest job search– that I’ve already vetted:

The 3 to 1 Rule


Credit: Brooke Cagle

When I moved to NYC without a job, I had a very short window of time to find work before I’d go broke and move back home to Ohio.

At this point in my career, I’d had an internship and an entry-level advertising job– but not much else. Entering into one of the most competitive job markets in the country brought about something I’d never experienced so much of all at once: rejection.

A few weeks into my job hunt, I made a rule for myself: for every rejection or piece of bad news I encountered, I’d do three things to counter it.

For example, if I got one of those boilerplate emails informing me I wasn’t a fit for the role, I’d spend the next hour applying for another job, follow up on another application and send a LinkedIn message to someone whose job sounded interesting.

The reason this works?

It keeps you moving forward and countering something negative with several positives and eventually this 3-to-1 rule will lead to good things. If adversity motivates you, this is a great strategy.

Like Frank Sinatra said: “The best revenge is massive success.”

This is your new job (or second job)

One trap that I see job seekers falling into is treating their job hunt as a vacation and not taking it seriously. Sleeping in until noon. Staying in pajamas. Falling out of shape. Working inconsistent hours. Netflix binging.

If you’re still employed, yes, you’ve had a long day but you still need to carve out consistent time if you want another offer.

It can’t work any other way.

You don’t need to wake up at 6:30am like you used to, but it’s really helpful to build a routine. Maybe you get up at 8, hit the gym for an hour and are online and applying for jobs by 9:30. You make lunch at noon. You block off 1 to 3pm specifically for following up on jobs. You block off 3 to 4pm to reach out to people on LinkedIn. You take a break for dinner and are back online for an hour around 7pm to check your email and save jobs you’ll apply to in the morning.

If you’re still employed, maybe you do start getting up at 6am and spend an hour applying for work. Hit a coffee shop on lunch break to send out more applications and use your evening to visit a meetup for other graphic designers where you might meet someone hiring. Cut out the Game of Thrones/Call of Duty/basketball watching until you’ve found the right job. If you’re willing to put in the work, it’s a litmus test for how serious you are about changing your future.

What some call “time chunking”, or breaking tasks into specific time periods and focusing solely on those tasks, can be effective. If you spend an hour solely focused on finding and saving jobs to apply to in the next hour, I guarantee you’ll be more effective than if you spent that hour answering emails, finding new job posts, checking Twitter and finding networking events. Your attention span is far better and you’re more productive.

It also makes you get out of bed, take a shower and know that your day has a very clear purpose even if there’s no need to be at the office.

Find what motivates you

Kelly Brito

Credit: Kelly Brito

This is a big one.

Without focusing on motivation and rewards, job hunting can feel a lot like punishment.

That’s why it’s important to figure out what motivates you, both on a micro and macro level. Perhaps it’s telling yourself that, if you get an interview lined up for next week, you’ll treat yourself to Chipotle on Friday afternoon. Maybe if you spend the morning cold emailing 15 hiring managers you’ll take a break at noon and go to the park for an hour.

There’s big picture motivation, the long term goals you’re working toward. Once you land this job you’ll book that Costa Rica trip you had planned before the layoff happened. Or once you’re in the position for six months you’ll buy your kids new bikes, just because. Perhaps you’ll donate your signing bonus to a homeless shelter.

Yes, if you’re looking for work your new full-time occupation is finding a job– but don’t forget about self care. Will you actually interview well if you’re burnt out and feel unrewarded? Will you be effective if it’s all stick and no carrot?

Keep these motivations in mind. Write it down and put it on a piece of paper in front of you. Put your goals on your phone background.

Make sure you have a combination of short-term achievable goals (sending out 15 emails/applications per day, attending 2 networking events per week, etc) and long-term goals (getting an interview, getting a second interview, getting an offer). If all your goals are long-term and distant you won’t feel like you’re making progress, even if you are.

When you win, whether it’s a great conversation at a job fair or a signed offer letter, celebrate and recognize how you reached that win.

Set Your Targets

One of the most difficult parts of job hunting is quantifying how well you’re doing– and if what you’re doing is effective. I often work with job seekers who say they spend hours each week on their job search, but don’t feel like anything is coming from it.

That can feel demoralizing quickly.

The trick is figuring out how much activity you’ll probably need in order to land a job, so I employ a strategy I used while working in sales.

An examples goes something like this:

If I send out 50 applications and 20 LinkedIn messages, I estimate I’ll receive 10 responses.

If I get 10 responses, I believe 4 of those will turn into interviews.

If I can turn 4 of those responses into interviews, I’ll be invited to a second interview with 2 companies.

If I can get two second interviews, one should lead to an offer.

Everyone’s numbers and techniques will be different and it might take time to figure out what your numbers are, but the advantages of this strategy are twofold:

  1. You can quantify how much you need to do to consider that day or week to be “successful”. If you’ve been job hunting for two months without an offer it can feel like failure– when in reality your small efforts are building up to a huge payoff; you may get three offers in the next week from work you put in two months ago. When you’ve hit your daily “quota”, consider that day a small win and take a short break to do something you enjoy.
  2. You can quantify what works and what doesn’t. Let’s say you spend an entire week sending applications through HR portals and you DM a few people through Twitter who have jobs at companies you’d like to join. Perhaps two out of fifty HR portal applications lead to an interview– but three out of four Twitter messages lead to an interview. By identifying which methods work through tracking results you’ll figure out the best ways for getting an interview and, eventually, an offer.

Like any good salesperson (because that’s exactly what you are while you’re job hunting), you’ll want to try different strategies. Spend one day sending out resumes with a short cover letter and another day sending out a more in-depth cover letter. Track the responses. Change the tone from formal to casual in your initial email. Track the results.

And if you’re looking for new ways to apply for work, I have a few tips here.

Don’t go it alone

startup stock photos.jpg

Credit: Startup Stock Photos

This one has always been tough for me. If I’m looking for work, I feel it’s up to me to stay consistent, apply for jobs, prepare for interviews and accept an offer.

That’s true. Nobody is going to find you a new job without your involvement.

But that doesn’t mean you can’t involve others in your job search. Support and encouragement can be massively helpful, whether that’s some constructive venting to a buddy or having a former manager work through a few interview role plays with you. This is where a career coach can be of help.

If your last job ended alongside a few other coworkers, set up a job hunting group. Get together at someone’s apartment, bring some snacks and get competitive with who can have the highest activity throughout the day. Encourage each other when there’s bad news– and good news. Work together to prepare for interviews. Bounce ideas off each other. Attend networking events with your crew.

Think Guardians of the Galaxy meets LinkedIn.

Make a list

There are plenty of well-documented reasons writing out goals and ideas is helpful.

One of my favorite positivity exercises is keeping a list of all the good things that happen throughout the day and reflecting back at the end of the day. If you get in the habit of focusing on the three negative things that happen during your day while job searching you’re unlikely to notice the six positive things that also happened.

Keep a notepad next to your laptop and write down the previously-mentioned goals and motivations every morning. And then jot down the good things that happen that get you closer to those goals– even if it’s as simple as “I got out of bed today and took a shower!”.

Eventually these lists will go from “I applied to 7 jobs today and got retweeted by an industry expert!” to “I negotiated an extra 4 vacation days into the contract at my fabulous new job!”

Focus on the positives. Learn from the negatives.

Beware of social media

Erik Lucatero

Credit: Erik Lucatero

“Don’t compare your behind the scenes with other people’s musicals.”

If I knew where I first encountered this saying I’d happily give the person who wrote it credit– but I can’t recall. It’s the perfect analogy for how we experience our own lives and view the lives of others on social media.

While you’re sitting there in your underwear considering applying to a job that pays less than your first job out of college, it’s easy to pull up Instagram or Facebook and start comparing.

Your old coworker just bought a new boat. Your ex-boyfriend is backpacking through Cambodia. Your friendly rival from college has two cute kids and makes a killer living writing a smoothie blog.

But that’s what they’re sharing. For better or worse (probably for worse), we’ve all become quite good at being our own highly self-aware PR agencies, posting only curated content that gives us the most Pinterest-looking lives possible. What you’re not seeing on Facebook or Instagram from these same people are their struggles– and they surely have them.

Your buddy with the boat? Maybe he bought the boat with an inheritance from a close family member who passed away and he’d much rather have them back than the boat. Your ex-boyfriend? Maybe he’s having a really tough time with homesickness. Your friendly rival? Maybe their kids were up with the stomach flu last night.

This is the behind-the-scenes stuff nobody shares.

So while you’re sitting on your couch either unemployed, underemployed or unhappily employed, realize that these people have bad days and struggles exactly like you do; a quick audit of your own social media feed of fabulous times with less than fun back stories prove my point. We all do it.

Help others

For a variety of reasons, helping others is hugely beneficial for our mental health and well-being.

During a job search it can feel most important to put the oxygen mask on yourself before helping others. It’s wise to spend time on your search and make sure you’re not diluting your time with distractions, but if you’re feeling down helping others may be the solution.

There are plenty of volunteer opportunities, whether it means delivering meals to seniors through Meals on Wheels or mentoring a more junior person in your field. Stopping by to chat with a sick neighbor and offering to do their grocery shopping could make a world of difference– for both of you.

Try putting an offer out on social media asking people how you might be able to help them. See what happens. I’m confident nobody has ever helped another person without feeling more positive.

Here’s the good news

A job search isn’t an end, a failure or a death sentence. It’s a change of plans, a fresh start and an opportunity to take control of your life.

It’s quite rare when we can step back, look at the future and have such a direct ability of shaping what comes next. We live in a time of direct access to people all over the world, tools and opportunities that make traditional employment unnecessary and you don’t need to be a well-connected Ivy League grad to find a job.

With the right tools, strategies and attitude it’s very possible you’ll look back at this transition as one of the defining (and best) forks in the road life presented to you.


Featured image credit: rawpixel.com









At Least 7 New Ways to Look For Work (That You Haven’t Tried Yet)

Hitting up your local newspaper classified ads is probably not going to land you the job you want– if any job at all.

(Honestly, the days of newspaper job ads have probably been gone since people were wearing Members Only jackets unironically.)

But as I work with entry-level job seekers, I hear my clients using a strategy that is almost as ineffective: sending out hundreds of blind applications to companies’ hiring portals, hoping to hear back.

And as a caveat, companies do hire from these portals. For some organizations, it might be an internal policy to field every application through this portal to keep things tidy, fair and legal. And you should keep an eye on these portals and apply without making them your sole focus.

If you’ve ever sent out dozens of applications through these portals, you’ve probably had the feeling you were throwing your résumé out into a cold, uncaring universe, hoping for a call back if the stars align. And you may not be far off.

Many of these portals use a keyword scanner to identify relevant skills and experience– or a busy recruiter or HR person reads through them individually. Some studies have shown a recruiter spends just 6 seconds scanning a résumé before moving onto the next.


Sure, you might be the perfect woman for the job but if the keywords didn’t generate interest or the recruiter has a stack of sixty-seven other applications– what then?

You need a new strategy.

When I used to work for a NYC staffing agency, part of my job was to find clients to place our talent with. One of the best methods for finding new clients was to find a need. In other words: who is hiring and what position are they looking to bring on?

In the case of a job seeker, by using alternative strategies to find who is hiring, you’ll stand out and not end up as just another application in a stack. It’s going to take some thinking outside of the box, some rejection and getting out of your comfort zone, but these seven new ways of finding work will have a huge impact on your job search and career.


Try your network

Your network is easily your most powerful and helpful place for finding work because you have a personal relationship and rapport with these people. And when I say network, I mean every co-worker, brunch partner, friend, neighbor, pick-up basketball teammate, yoga buddy and family member you have.

They don’t need to work in marketing or be an engineer or own a business relevant to what you do. They don’t have to be a recruiter or know anyone hiring right now.

But simply making it known that you’re looking for work can open up doors. In fact, it’s a very similar strategy that business networking group, BNI, employs to help its members: it’s not who is in the room, it’s who the people in the room know who may be able to help.

Obviously use your discretion. If you’re in the middle of a discrete job hunt your employer can’t know about, maybe try the circle of people you trust the most with sensitive info.

Drop a text or make a phone call to someone who may not know you’re looking for work. InMail your buddy from that job you had in college who looks like he’s working for an interesting company. Offer to buy your neighbor a coffee and see if any of his buddies he plays cards with know of an opening.

Expand your network


“But I don’t know anyone who can help me,” you might be thinking.

Maybe you just moved to a new area. Maybe you don’t speak the local language. Maybe your friends and family make their living raising goats or are all employed with NASA and their only friends are also slinging goat cheese or shooting stuff into space.

No worries. It’s time to find people who are more in line with the job you have in mind and that means something that will strike fear, anxiety and hate into the heart of every introvert and many others: networking.

Networking is a lot like swimming: you fear it until you do it a few times. I’m on the line between an introvert and extrovert, so don’t think this advice is coming from someone who hops out of bed at 6AM and excitedly makes small talk over muffins.

But networking really is the way to expand your professional network. 

There are plenty of options: Chamber of Commerce meetings, Young Professionals mixers, trade and industry-specific meet ups. There are a crazy amount of events happening and I’ve used MeetUp to find them.

It doesn’t even have to be a professional setting. Join a free softball league, go volunteer at a homeless shelter, invite all the neighbors you haven’t spoken to in 7 years over for a bonfire or strike up a conversation at a coffee shop. Bring a buddy along.

Networking when you have something you want can sometimes feel greedy or self-involved, especially when you’re meeting new people specifically to find work for yourself.

It doesn’t have to be that way. One of my favorite things to do in a networking situation is ask the following questions:

• When you come to these types of events, who do you hope to run into or meet?

• Can you tell me more about what you do?

• What’s the best advice you’ve ever received while networking?

Sometimes you might know the perfect person to introduce this person to– or you may just make their day by expressing interest in what they do or know. I’ve begun making an honest effort to provide value to others whenever I can and people seem to appreciate it.

Use your social media

Sure, your social media channels might be full of cat pictures, memes and heated political debate, but there’s still value here and it’s twofold:

You can use social media to alert people you know about your job search and what you’re looking for. You can find people at companies you want to work for and easily reach out to them through messaging. You can create cool content showing your value– and someone might notice. Social media is amazing for communicating thoughts, ideas and breaking down barriers that used to separate the hiring from the hopeful hires. Don’t hesitate to direct message a hiring manager or HR Director; you’ll definitely get ignored, rejected and maybe told to “just apply online like everyone else” a few times, but someone will find your proactive approach interesting.

Alternatively, keep people in your city aware of your availability:

“Anyone CD’s in #Austin looking for a #copywriter? Experience in beauty, auto & tech clients. Check my portfolio here: (Bitly link)”

Maybe less obvious than using social media to communicate is using it to gather data. You can absolutely use social media to find who is hiring and even predict it! That cool startup in town just mentioned on Twitter they’ve secured funding? Guess who WILL be hiring within days or weeks. Many, many times each week I see requests for certain professionals or skill sets on social channels.

Another outside the box idea: search hashtags relevant to your profession. Maybe someone is having trouble with #Excel and you’re a spreadsheet god? Maybe a recruiter just posted an #accountant position you’d be perfect for? Try narrowing it down by location, hashtag and get creative.

Assuming your job search isn’t a total secret, use social media frequently during a job hunt. Don’t become that guy who vents on his Facebook about how frustrated they are about an interview that didn’t pan out, but stay active on industry LinkedIn groups, retweet relevant industry news on Twitter and keep people posted about what you’re looking for.

And keep in mind: new employers CAN see your social media, often even if you’re set to “private”. Post accordingly.

Bonus points if you run an ad on social media advertising your experience or service. Extra bonus points if you use social media to cold email or message someone and ask them to meet and discuss the company or open positions.


Market yourself like a product

Job hunting is no different than selling a product– except that you’re a sentient being doing your own marketing.

So do what the pros do and get into content marketing. If you’re not of a sales or marketing background, one of the biggest names in the content game, Hubspot, explains content marketing this way:

What is content marketing? Content marketing is a strategic marketing and business process focused on creating and distributing valuable, relevant, and consistent content to attract and retain a clearly defined audience, and ultimately, to drive profitable customer action.

It may not be necessary to create workflows, email campaigns and use software like in a traditional content marketing strategy, but let’s focus on what this is suggesting you do in a job hunting sense:

Create valuable, relevant content (videos, blogs, articles, podcasts, etc.) that speaks to the decision makers of your industry and drive them to offer you an interview and then a position.

So what does this look like?

Recently, I worked with someone who had been out of work but was using some of his free time to create how-to videos on software used in his industry. I encouraged him to share this across all of his social channels; you never know who might love what you’ve written and decide to reach out and form a connection. Again, maybe they’re not a hiring manager– but it’s an additional means of growing your network.

My recommendation is to start a simple WordPress site or a Medium account. Start writing. Use Answer the Public to figure out topics. Ask your partner or friend to proofread. Publish your articles on LinkedIn, WordPress and Medium. Share them over your social media channels (Twitter, Facebook, etc) and forums.

The added benefit? If you’ve been off work for some time, this is a GREAT way to fill that gap on your résumé. Yes, you’ve been unemployed by an employer since February– but you’ve also been creating awesome articles and videos relevant to your career and industry. You have something to show for your time and you shouldn’t hesitate to list this on your résumé as relevant experience.

Align your interests with others

There are incredibly talented, brilliant and caring recruiters and staffing agencies out there. There are staffing agencies and recruiters out there who are exactly the opposite. Again, I’ve worked in staffing so I have a soft spot for these folks– but I’ve also been on the wrong end of recruiters.

Don’t let one bad experience you or your friend’s brother’s neighbor had with a staffing agency or recruiter sour you on the whole idea. Yes, staffing agencies and recruiters will be paid by the employer in the way of a nice bonus. Yes, it’s possible they’ll make a killing off your placement.

But that’s my point.

By working with a few recruiters or staffing agencies, you’re working with people who are going to get paid as soon as they find you work. Your interests are aligned in this specific area. They want to find you work. They’re going to work full-time trying to find you a position. And a good recruiter or agency will recognize that, one day, you may even hire them to find you a good candidate and become a client.

There are hundreds of agencies and recruiters out there, but having worked for a specialized staffing agency that had a rather narrow expertise, I’d recommend working with a recruiter or agency who is industry or job specific. They’ll likely know more about your role and have better clients to introduce you to than someone who staffs everyone from line workers to salespeople to writers.


And if you’re on the fence about recruiters or agencies, it’s fine to politely let them know you’re apprehensive. Good agencies and recruiters will understand and probably have great reviews online and evidence of their success. Use your gut when deciding who to work with and, if possible, use that network to find a recruiter.

Create your own job

Maybe this career change is exactly the push you’ve been waiting for to finally take your prototype product and start shopping around for vendors. Or maybe it’s time to begin working on a consultant or freelance basis.

Whether it’s to keep the bill collectors from calling as a way of generating income while you search or to actually start your own business, during a job transition you may find yourself in the perfect spot to create your own position.

Entrepreneurship isn’t for everyone. Financial pressure, unknowns and patience may make it a difficult time to transition from job seeker to business owner while out of work– but keep the option open. It’s unlikely you’ll soon have this much free time to learn, grow and build something.

If you’re still in your job with steady income rolling in, it might be the perfect time to start working after hours to prepare for this move. Entrepreneurial guru, Gary Vaynerchuk, is actually quite adamant about only starting a business with either serious savings on hand or a full-time job to help stay afloat.

Stay proactive and ready

The best time to look for work is when you don’t need to.

Even if your company is rock solid and you have job security for the next 10 years (you think!), be active in your career. It’s easy to fall behind trends, dig into a 50 hour work week and collect a paycheck.

Have informational interviews when a company reaches out if you can do so without jeopardizing your job. Know what’s happening with your competitors and peers at other companies. Stay active on social media and be a whatever-your-profession-is that people know about. Go to networking events. Write articles. Take classes.

Keep your résumé updated– always– so you don’t need to think back three years to what the exact figures were on the project you lead that made the company millions and got you a raise.

You may have no intention or plan of leaving your job, but if the last two decades have taught us anything at all it’s that even the most concrete plans and careers can change. You’ll be better off if you’ve been in “career mode” without the pressure of needing a paycheck.

Job hunting is like fishing

Did you ever go fishing when you were a kid? If you were like me, you probably dropped a single soggy worm on too short of a line into a murky pond and didn’t catch anything.

And that’s what people do when they’re looking for work: they rely on one really bad, singular method.

Whether you’re fishing or looking for a new job, you need as many lines and hooks in the water as possible; your friends, recruiters, alumni contacts, traditional job portals, networking meetings, article-writing, social media activity are some of the best tools you have.

You need to use different baits, ask for advice, try crazy ideas and do everything you can to increase the chances that someone– or something, in the case of fish– is going to bite.

I’m confident that these 7 new strategies are going to invigorate your job search.

And if you’re looking for more ideas, guidance, or advice, don’t hesitate to contact me for help!

Photo credit to Matthew Henry.



4 Big Reasons You Need a Career Coach For Your Next Job Search

I was always a personal trainer skeptic.

I’d go to the gym, lift weights and try to figure out what the machines did. And it showed: the results were underwhelming.

When I moved back to Ohio after years in NYC, I went from walking ten miles each day to ten miles per month. I tried to eat healthy. I tried to hit the gym on my own. Pretty quickly, however, I had to figure out something else as my waistline expanded– and I didn’t have the tools or knowledge to turn it around.

So, I hired a personal trainer.

I’ve never thought of myself as the type of person who hires a personal trainer and I figured I’d need to start shopping at Lululemon (or wherever men buy expensive active wear) and put kale and whey protein on everything.

Instead, I worked bi-weekly with an expert who not only passed along his incredibly valuable knowledge and helped me get results, but also kept me motivated. When another set of squats felt impossible, he was there to talk me through it and how to work on my technique. When I wanted to cancel because I was still sore from yesterday’s workout, he held me accountable and gave me pointers on food intake. His expertise, guidance and motivation helped immensely.

During our few months of working together, I’d learned more about fitness than I had throughout the rest of my life. I could hold a plank longer, lift more, bike farther and felt amazing. 

I thought about how my gym lessons could be applied to my personal and professional life and an idea began to formulate. I’d worked for a top creative staffing agency in NYC and over the past few years I’d very accidentally started mentoring entry-level job seekers based on a few Reddit and Twitter posts I’d written.

As more and more people started to reach out and I spent time working with a personal trainer, the worlds merged:

Why don’t I help people with their job hunt in the ways my trainer helps me with my fitness?

I’d had some very successful, short job hunts. I applied what I know about sales and marketing to the job search. I’d been an active part of dozens of clients and candidates exploring the hiring process while working in staffing. I knew what hiring managers loved, hated and wished candidates would do. And this information didn’t seem to be reaching university classrooms.

(For all the time we spent learning about the Pythagorean Theorum and Shakespeare you’d think they could’ve mentioned how to look for work, right?)

A career coach is a personal trainer for your career

Both a career coach and a personal trainer offer their time, knowledge, strategies and motivation to achieve goals.

For example:

You know how there’s that ONE interview question you always bomb and hope they won’t ask– but they always do? A career coach will role play that exact question with you, finding the best way to answer truthfully and strategically.

You know how your aunt told you it just takes showing up in a suit and applying in person to get a job? A career coach encourages you to find methods that really work in 2017.

You know that thing you really don’t enjoy doing when looking for a job? A career coach encourages you to do it anyway if it’s effective, plus helps find a few ways to make it suck less.

And just like a personal trainer, working together through repetition, practice and strategy makes you stronger– and builds skills you can use longterm.

As I watched the folks I’d worked with go on to receive job offers and internship opportunities, it solidified the idea that there just might be something to this career coaching thing.

The more clients I worked with on their job searches, the more I began to realize a few important aspects of why career coaching should be more of “a thing”.

Employment is changing

As employment transitions into what experts call “the gig economy”— short-term, project-based and freelance employment not tied to one main employer– it will be increasingly vital to know how to get work quickly and predictably. While the idea of having to look for a job frequently may sound overwhelming, these skills can be learned and taught by a career coach.

In the world of freelance it’s already known that those who make the most money aren’t necessarily those who are the best at what they do– but rather those who can close the deal and get the work.

I spent four years in high-pressure sales roles. I found very quickly that what I’d learned in sales training had direct applications to job hunting. In both instances you’re trying to help your client navigate a need or issue– and you need them to choose you, often in exchange for tens of thousands of dollars. Persistence, positioning and strategy come into play in both areas and the lessons I learned in sales training (and on the job) I pass along to my clients.

Job hunting skills are rarely taught

For the majority of clients I’ve worked with, job hunting wasn’t covered in their K-12 or university coursework. If it was, the lessons were basic and outdated. There’s so much more to know than just putting together a spell-check résumé and hoping it lands on exactly the right hiring manager’s desk– but that’s all most of us are ever taught, if that at all.

I was lucky to have a few great professors at Kent State who did spend time helping us with interview etiquette and résumé writing– but there’s no replacement for one-on-one coaching, role playing and being tuned into amazing technology available to job seekers.

Unfortunately universities are happy to turn out well-educated, informed students– but often fall short in the step of giving them the skills to actually win the job offer.

Looking for work has evolved in the past 5, 15 and 50 years– immensely

Because I primarily work with younger, entry-level job seekers, I run into advice given to them by professors and parents. Some of it is wonderful guidance, given from years of experience and wisdom mixed with up-to-date knowledge. Sometimes, it is advice that should’ve been left behind during the Carter presidency.

And it’s no fault or bad intentions of these parents or professors, however, the job market has shifted greatly– and along with it, so has technology, techniques and etiquette. It simply doesn’t make sense to type out a cover letter for a UX role at a cool startup, drop off the application in person and then show up to the interview in a suit and tie. Nor does it make sense to only rely on job posting boards when half of all job openings aren’t even advertised.

It’s a career coach’s job to stay up to date with new technology, new platforms and new ideas. I stay in touch with multiple recruiters, listen to their feedback and candidate stories to see what’s fresh. I read blogs, follow folks on Twitter and strategize new ways and methods of helping my clients. It’s my job to dispel myths and help job seekers use what’s current for 2017 to nail that interview or negotiate their salary.

Changing jobs is inherently stressful

There’s a reason why the top 43 most stressful life events on the Holmes-Rahe Stress scale are littered with events surrounding work and employment. Even if the job search is warranted and wanted, uncertainty around change can be difficult to manage. If the job search is unexpected or unwanted it’s even more difficult as our finances– and ego– take a hit.

I worked with a client recently who’d been unemployed for months. He’d applied to dozens of jobs in the past few days. He felt he was doing everything he could to market his valuable skills– and yet he rarely received an interview. Understandably he felt depressed and hopeless.

From our hour long call, we discussed new strategies for attacking his job hunt more effectively, but I also spent time boosting his confidence about his qualifications and how his perseverance will pay off. Job hunting can be lonely– but it doesn’t have to be.

Work– and the time we spend at work– is important

Assuming we work full-time from ages 22 to 65, we’re spending 43 years of our lives working.

If we’re working 49 weeks of those 43 years at an average of 47 hours per week, we’re spending 99,029 hours doing something we should enjoy or, at the very least, find acceptable. It’s no wonder that as Millenials take up more and more of the labor market we’re asking for better work/life balance and work that matters.

If you’ve just graduated college, are navigating your first jobs after graduation or are looking to transition from your current role, I’d love to set up a time for us to chat. If you don’t know where to start on your job search, this is the perfect jumping off point, starting with an always 100% free consultation to understand where you are and where you want to go.

Let’s chat soon.


Photo credit to Marc Mueller.


Instagress is Dead– but My Love for Instagram is Revived

Last week, I began seeing rumblings that beloved Instagram “bot”, Instagress, was offline. Posts on Reddit anxiously mentioned clients’ Instagram traffic slowing drastically, the site wasn’t working, their Facebook page disappeared– and then Instagress announced the shutdown. I’m open to correction here, but it sounds as if Instagram didn’t take too kindly to Instagress violating Instagram rules.

I used Instagress to build my Instagram following and wrote about it at length recently. I went from around 600 followers to over 7,000 in about 9 months, engagement was high and I used it to build a following to sell watches. It worked!

Mostly. Technically.

I auto-liked pictures of peoples’ kids in the Phillipines and guys standing shirtless in front of a bar somewhere in Poland. I auto-followed every awful luxury-lifestyle-motivational-quotes account and began missing posts from people I really did want to follow.  I was one of those commenters on your Instagram: great shot, keep it up, where was this taken, etc.

Yes, I was driving traffic and sales. Yes, my KPIs were strong. But didn’t I once use this for enjoyment and fun?

Luckily for me, my credits on Instagress were set to run out around the time of the shut down anyway. Even before I knew of the shut down, I was debating about renewing my time block. I’d begun deleting as many obvious bot posts on my own photos. Instagram began to feel like a chore. I was missing out on comments and posts from friends.

Once Instagress shut down, I watched my metrics begin to tank, followers drop off and began looking for a new solution to stave off the losses. But just as quickly as I started the search, I stopped. Let’s make Instagram great again, I thought.

Since then, I’ve gone from 7,050 followers down to 6,994 and dropping, feeling strangely connected to that Black Mirror episode with Ron Howard’s daughter and her social score.

But I’m also enjoying Instagram more than I have in a long time. The interactions are real, the followers are organic. I can comment on a photo, not worrying that I’m about to over-comment for the day and get banned, and actually interact with people. I can “binge like” my cousin’s baby’s photos she posted.

It makes me sorry for the brands and agencies that used bots as a product with huge benefits. They’re useful and effective, in general. But I won’t be entirely sad to see them go away and I imagine that Instagram will eventually chase out every single one they can, focusing more on selling Instagram ads and sponsored posts.

What Instagram could do, however, is work to build an ecosystem of influencers if they haven’t already started. Put their top influencers in touch with relevant brands. Make suggestions on how to increase engagement. At this point it’s no secret that brands and people are using Instagram, so why not help people capitalize on it and remove the motivation to use bots?

As I write this out, I realize just how funny and skewed technology can make what should just be a simple, artistic pleasure. For those of you using Instagram bots (or those who hate them!), what’s your take on Instagress and the future of Instagram advertising?


13 Tips for Crushing Gary Vee’s 2017 Flip Challenge

Now that we’re almost 4 months into the #2017flipchallenge, it’s a good time to step back, reflect and see what’s working– and what isn’t.

I’ve learned, lost and won over the past few months and I’m happy to share a few tips I’ve found that work for hitting that $20,0170 goal.

Check it out!

What to sell

• When selecting items to flip, consider one of the basic models of economics: supply and demand. High-supply, low-demand items will always perform the worst. Low-supply, high-demand items are money magnets.

• Build an inventory of easy to ship, lightweight objects. Sure, maybe that vintage lamp just sold on eBay for a good chunk of change– but if you’re spending big money on shipping you’ll eat away your margins.

• Sell what you know. I know about watches and cars– so that’s where my focus tends to be. It wouldn’t make sense in time or risk for me to branch out to, say, porcelain dolls or broken iPads. If a new item you’re not familiar with does strike a curiosity, go for it– but be sure to learn more before investing too much.

How to sell it

• Is an item not selling? Try offering free shipping and pad you price to compensate a bit. Sometimes that trick of psychology will make the sale for you.

• Is an item still not selling? Try bundling it with a similar item. This not only makes it look like a better deal, it also saves you time on listing multiple items.

• And if it’s still not selling, make sure your price is in line with similar items by checking “Sold” auctions on eBay. Ensure it’s posted on multiple auction or selling platforms. Play with copy and descriptions. Make an effort to sell the item in your listing; what problem will it solve for this person or what value will it add to their lives?

• Use every platform possible for selling; the more channels to sell through, the better. LetGo, OfferUp, eBay, Craigslist, Facebook Marketplace and Instagram are some of the best bets.

• But use the platform that makes sense. If an item is large or expensive to ship, Craigslist or LetGo might be best. If an item has specific appeal (clothing, hobbies, collectibles, etc.), eBay is you best for attracting buyers.

• If something has a very specific appeal, go straight to your target market on a forum. If you’re flipping a horse saddle you picked up on Craigslist for $20, find the most active farm or equestrian forum you can and post it in their classified section. Chances are if there are collectors, hobbyists, enthusiasts or otherwise there’s at least one active forum.

What to do after you’ve sold it

• Shipping books, DVDs or CDs? Use Media Mail through USPS to save on shipping costs.

• Buy shipping supplies in bulk. Tape, bubble wrap and envelopes can add up. By visiting a wholesale club or Amazon you can score huge quantities of supplies for much less.

• Stay organized by tracking your cost, selling price, shipping expenses and more. Check out the helpful spreadsheet at the end of this post I shared a few weeks ago.

• Remain positive. It’s easy to get disappointed when you’re having a slow sales week, but keep trying new strategies and keep a steady flow of inventory coming in. Use data and numbers to influence what you buy and sell, for how much and through which channel.

Keep on flipping

Flipping is one of the most enjoyable, easiest ways to try out entrepreneurship and the Flip Challenge is the perfect introduction.

What tips and tricks do you have for crushing Gary Vee’s 2017 Flip Challenge?