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Interview with a Successful Startup Founder

Bootstrapping a Startup Agency to 40 Employees

Andrew Verboncouer
Andrew Verboncouer
October 19, 2021
Category of startup
Country of startup
United States
Revenue of startups
No Data
Interview with a Failed Startup Founder

Bootstrapping a Startup Agency to 40 Employees

Andrew Verboncouer
Andrew Verboncouer
October 19, 2021
Category of startup
Country of startup
United States
Cause of failure of the startup

Andrew co-founded Headway, a company that works with startups and corporate innovation teams to discover, validate, build, launch, and grow new ventures. In the last 6 years, they have grown from a 4-people team to over 40 full-time crew members.



Hi Andrew! Who are you and what are you currently working on?

I’m Andrew Verboncouer, a 35-year-old entrepreneur and designer based out of Green Bay, WI. I’m one of three partners at Headway, and we’re helping create services, products, and communities that help founders launch and grow startups.

Headway is a company that’s focused on bringing entrepreneurial ideas to market and keeping them there. We work with startups and corporate innovation teams to discover, validate, build, launch, and grow new ventures.

Headway Office

I’m currently Partner & CEO at Headway. Still, I have played many different roles as Headway’s grown, including Head of Design and Head of Product Strategy, in addition to contributing to some projects on both front-end and back-end development. 

My main goal for Headway is to align our team and capabilities with partners who have strong ideas that are loosely held and want to increase their chance of success by using research, design thinking, and continuous learning to create experiments and gather evidence that helps make better decisions.

What's your backstory and how did you come up with the idea?

Before Headway, my partners and I worked with other startups as Co-Founders, Partners, and consulting with startups. 

Headway came out of a passion and desire to create new things and new ways of doing things. It was also born out of just a gap we saw in the market of how companies were showing up to serve startups. We started as a way to partner and own problems alongside other founders. 

Working with passionate founders who have an idea, a vision, and a future impact they want to make is so energizing.

When we were raising for our previous startups, we needed folks to join us to help us go faster because our vision outpaced our velocity. In that process, we only found vendors and not trustworthy partners. They would ask questions about specific requirements, hardening scope, fixed procedures.

But that’s not how startups work. There are so many unknowns, so many surprises, and so much uncertainty. 

What we wanted was a partner to take ownership alongside us and help us learn and adjust with the market, figure out how to gain best and serve customers, and care about it as much as we did.

Headway Video Call

I went to college for Business Administration and MIS and was a self-taught designer, mostly from experience doing projects out of passion or friends. 

Since high school, we were always creating new things - not for profit, but for fun. We started snowboarding clubs, t-shirt companies, we sold lip-synced mixtape videos long before YouTube existed. Along the path, as we were designing and creating, we evolved from doing websites and e-commerces to full-fledged applications. 

Eric, Partner & COO at Headway, is also my brother. In the earlier days of our journey, we started our agency called VERBS, and within that agency, we did all things for all people. With that approach, we had enough work to keep us busy and had the typical freelancer mentality. 

When we started Headway, we knew that to grow beyond ourselves we had to find a more targetable niche to attract clients more predictably, know where to find them, and find people who could join us on the journey. 

Throughout our startup journey before Headway, we were part of so many different efforts—some that failed miserably, some that were sold, some that are still in the market today. In the worst-case scenario, we built the product in isolation for a year and a half and didn’t talk to a single potential customer.

To our surprise, it failed without any traction at all. We tried to save it by pivoting with the market, but we were out of resources, and more importantly - our energy and enthusiasm for it.

We ended up creating something that no one truly wanted. This was all before Lean Startup, but we started moving into our next startups by creating prototypes, validating with our customers, and having honest conversations around their problems.

That’s where we started shifting from building products to building prototypes and using them to sell into both B2C and B2B opportunities. We wanted to bring this validated and continuous learning to the struggling startups so they could start making traction and get real-world business progress.

Which were your marketing strategies to grow your business?

We’ve grown through long-lasting relationships, partnerships, referrals, and word of mouth as most service-based businesses. 

We’ve been starting to put concerted effort and investment into things that attract customers and also things that can help us identify and reach out to them.

Headway Office Hours

When we started Headway, we didn’t leave our full-time jobs and focus on it until we could sell our first customer on a product team coming alongside them. It consisted of 3 engineers and 1 product designer/strategist.

We’ve grown our revenue through increasing rates and starting to niche down from anyone who can use our services to particular offerings. We haven’t figured it all out, and we are constantly experimenting.

How are you doing today and what are your goals for the future?

Headway has been growing consistently since we were 4 people back in 2015 and are now just shy of 40 full-time crew members.

We’re structured across departments that collaborate in cross-functional teams: Sales & Marketing, Design, Strategy, Development, HR/Admin.

The last two years, we’ve been named one of America’s fastest private companies on the Inc. 5000, coming in at #912 in 2019, and #2765 in 2020. 

We plan to continue growing our impact and diversifying our revenue by moving from services only to more scalable and affordable options that include productizing our knowledge, approach, and tooling.

We are currently working on new ways to serve startup founders to help them go beyond our core services. Be on the lookout for new offerings like founder cohorts, startup coaching, and more.

Since starting Headway, what have been your main lessons?

There are three main lessons I’ve learned since starting Headway. 

  1. People are at the center of everything. Being a founder means that you always have to be selling. And not sales in a slimy way. But sales by educating, clarifying, and communicating in a way that resonates with people. I learned if you want to build a business, you have to focus on the people. That means being a person that other people can get behind. Being someone that people want to join and come alongside. And being somebody that people would like to work with, especially in services people buy from people. Understanding how you help other people get what they want enables you to achieve your goals. Being helpful, genuine, and caring about anyone I’ve come in contact with has helped me build deeper relationships and more meaning in our work.
  1. Clarity is power. If you're not clear, you can go in the wrong direction quickly. And when things are blurry, it's easier to get off track. So spending the time to work on clarity at every level is going to pay dividends. Because all things evolve, your company, your customers, and how you serve them also change continuously. I’ve learned that you have to strive for clarity continuously. We always need to ask, “where are we now” and “where are we going?” At Headway, we've implemented EOS (the entrepreneurial operating system), which helped give us clarity through cadences weekly, quarterly, and annually.
  1. Problems always exist. At first, your issues are massive. As a founder, you’re thinking about leaving your job; you’re trying to figure out if anyone wants what you have to offer. As you solve those problems, other problems emerge. You have clients, but not the clients you want or feel you can add the most value to. You have revenue but not enough margins to build the culture and benefits you want. You have people, but ones that aren’t enjoying all of the work you’re doing. The people who join your team and the clients you help on their journey will leave. It’s not an if, but when. As a founder, it's hard not to take either of those personally. There will always be problems, no matter what. If you understand that from the start, you can detach a little bit of emotion and negative self-talk that leads you to question yourself and the journey you’re on. When you’re a founder, and you’re a father or have a family you go home to at night, problems can prevent you from being present. You are more than what you do! All you can do is solve the problem to the best of your ability and continue to move forward with a plan that avoids/solves/deters that same problem in the future. I had a football coach who said the difference between good and great is a thin line that separates who can learn and build upon their learnings after the first lesson.

What were the biggest obstacles you overcame? What were your worst mistakes?

One of the biggest obstacles we overcame was making it to just before the 1-year mark. We had dwindling sales, and all of our contracts were running out. In August of 2016, we only had only two weeks of runway left. 

One of the 4 founding partners ultimately decided agency life wasn’t for him, and he left the company simultaneously. 

With our backs against the wall and only one full-time employee other than the remaining three partners, we had a “come to Jesus” moment.

We gathered in Eric’s basement bar, poured a drink, and said either we’re going to do this, or we’re not. 

If anyone else was out, this was their opportunity to hit eject. 

We all were in. We had a vision for what Headway could become and an appetite to bet on ourselves to make it happen. 

What tools & resources do you recommend?

For startup founders

We’ve created some incredible resources for founders and product teams.

Startup Foundations

A free video series we created to help startup founders to gain traction in the most critical parts of their startup. We teach proven tactics that will impact real business growth.

Founder’s Mindset

A free video series to help founders improve their mindset around launching and growing their startups. We’ve seen countless startups fail because founders didn’t have the right attitude. Learn the common mistakes we see and how you can give your startup a greater chance for success.

Headway YouTube Channel

We host live streams and release new videos every week to help founders and product teams improve how they work together, solve problems, and get actual results.

Business and team management

EOS - Entrepreneurial Operating System

We highly recommend checking out the EOS model to help guide your business growth and align your entire organization on goals that create impact. It gives entrepreneurs and leadership teams clarity on what to do next and how to solve issues through focus, discipline, and accountability.

Startup Employee Onboarding Process

The way you onboard new employees for your startup can make or break if they decide to stick around. We created a resource for founders to develop a clear onboarding plan and improve employee retention.


This is where we document all of our processes, resources, and essential information for our team and our clients.


We use Asana to manage internal business goals, projects, and experiments.


We have one-on-one meetings every week with all of our crew. This enables us to build stronger relationships internally, build trust, and solve problems before they get worse. LeadHonestly is an excellent tool for bringing up impactful conversations.

Where can we go to learn more?

You can learn more about what we do and access free resources for founders and product teams at Headway.io.


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