Troy Vosseller of Gener8tor: “It’s a Long Journey”

It’s a Long Journey. Being an entrepreneur is a long journey that has highs and lows. Don’t let one decision or inflection point determine the long-term outcome. It’s important to keep the business and your journey in perspective. A good motif I heard on this once was whenever things are going really well or really […]

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It’s a Long Journey. Being an entrepreneur is a long journey that has highs and lows. Don’t let one decision or inflection point determine the long-term outcome. It’s important to keep the business and your journey in perspective. A good motif I heard on this once was whenever things are going really well or really poorly, pull up Google Earth and zoom into your GPS coordinates. From there zoom out slowly to your city, then your state, country, and the whole world — the pin of your location becomes smaller. This puts into perspective how insignificant any one little action or activity is.

It’s a humbling experience that helps you realize that in the grand scheme of things, as long as your trajectory is positive and to the right, and you’re experiencing more highs than you are lows, that you’re achieving the net positive that you’re seeking.


Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Troy Vosseller.

Troy is the Co-Founder of gener8tor. Gener8tor’s turnkey platform for the creative economy connects startup founders, musicians, artists, investors, universities, and corporations. Gener8tor operates more than 45 accelerators annually across North America, working with more than 200 startups per year. Since its inception in 2012, gener8tor has worked with 500+ startups that have cumulatively raised $500M+ in follow-on venture capital.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My business journey began in my college dorm hall at the University of Wisconsin-Madison in 2004. (Go Badgers!) That’s when I started Sconnie Nation: a t-shirt company. This company was the most clichè college business you could think of, but the experience became the impetus of my entrepreneurial journey.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

My business partner, Joe Kirgues, and I were lawyers when we met. We were working on a mutual transaction together between a startup and an investor and hit it off personally and professionally. During that time, we saw an opportunity in the lack of coordination for an entrepreneur to go from idea to incorporation to growth to raising venture capital (VC). We wanted to make it more efficient by pulling all these resources together. We wanted to make small investments and bring mentors, customers, corporate partners, and investors together to help startups gain access to the resources they needed to continue to grow.

We had been admirers of the accelerator model that started with Paul Graham and Y Combinator and believed we could do that in Wisconsin, which is where we started gener8tor in 2012. We were fortunate enough to find a group of angel investors out of the Milwaukee area who shared our vision. That’s when we left our jobs as lawyers and decided to dive into gener8tor full-time.

In your opinion, were you a natural-born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

I knew I had the entrepreneurial bug during college when a friend and I would walk to class talking about business ideas all the time. We finally saw an opportunity to give it a go when we created our t-shirt company called Sconnie Nation. With $300 each of our own savings, we created and sold t-shirts that celebrated the Wisconsin lifestyle out of our dorm room. Within the first week, we sold out and realized we were onto something.

The college dorm room startup was the epitome of low-tech with screen-printed t-shirts, but the experience was the impetus of my entrepreneurial journey. This experience led me down the path of meeting my business partner, founding gener8tor, and eventually to how we host conferences today like our OnRamp Conference Series that connects corporations and startups.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

I come from a family of entrepreneurs. My grandparents on my father’s side were lifelong farmers in Iowa. We have a ‘Century Farm’ which has been held by our family for over 100 years. On my mother’s side, she and my grandparents immigrated from Italy to the United States and owned a tailor shop.

Throughout my childhood and for most of my life, my parents owned their own business. I didn’t grow up with parents who had a traditional job or career. They did everything from selling fitness equipment all the way to manufacturing a salt and sand spreader for ice control that was sold to colleges and universities.

I remember around Christmas time one year, my parents’ company was doing a direct mail campaign, and my parents, siblings, and I sat around the kitchen table stuffing envelopes and licking stamps. I was raised with the entrepreneurial spirit and it was very much ingrained in my mind.

What do you think makes your company stand out? Can you share a story?

At its core, gener8tor is a venture capital fund and a startup accelerator program. At the center of everything we do is our customer — the entrepreneur. It is the startup founder that we invest in, mentor, and work with. A unique part of our company is the OnRamp Conference Series where we connect startups with corporations within specific industry verticals. The genesis of this revolves around what our customers (the entrepreneurs!) want from us, which is venture capital, investment, customers, and revenue.

To give an example, the OnRamp Insurance Conference, which is our largest OnRamp vertical today, was developed as an efficient format to meet our customer’s needs. Over 50 insurance corporations and carriers send their corporate venture and innovation teams to meet with hundreds of startups for a one-on-one pitch meeting. This year about 500 startup applicants applied, and the opportunity is completely free for startups.

That list of 500 insurtech startups is shared with the insurance corporations and carriers who select their top dozen for a free one-on-one pitch meeting. During normal times, the trademark of this conference is that it’s held at sports stadiums and each insurance carrier receives their own suite or luxury box to host the pitch meetings. COVID moved all these OnRamp events into a virtual environment which created an even more efficient format and the opportunity to accommodate more insurance corporations and startups.

The one-on-one pitch meetings and connections between insurers, investors, and startups make our OnRamp conferences unique. In addition to insurance, the OnRamp conference format is one we have adopted for our verticals, including education & workforce innovation, healthcare, manufacturing, agriculture, entertainment, and impact.

You are a successful business leader. Which character traits do you think were most instrumental to your success? Can you please share a story or example?

The one trait I always point to, whether it’s colleagues, team members, or entrepreneurs, is something I would define as ‘insatiable curiosity’. This is someone who’s interested in going deeper than the surface level of what they’re working on. And even better is when you can do this unprompted. Be curious about what is happening. Read news articles or look at social media to see the latest in your industry and beyond.

When I’m interviewing an entrepreneur for potential investment, I often Google my interpretation of what they’re saying to see who their competitors might be. If I ask the entrepreneur about those top Google search results, I expect for them to have a credible counterpunch, reaction, or thoughts about that competitor that a layperson like me could find.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about the advice you’ve received that you now wish you never followed?

When entering venture capital (VC), I was told the industry prides itself on originality and on growth. However, I don’t think the industry itself has done much to evolve. The profits a VC makes are a throwback to shipping cargo. The notion of carried interest is a holdover term where the owner of the ship would get a percentage of the cargo on that ship. The term is outdated, but even the concept is rather rigid. There has not been a lot of evolution, innovation, or creativity in exploring new and different VC business models.

Another area is growth. As a VC at gener8tor, we push our startups to grow and we believe startup equals growth. If you’re not growing as a startup it’s probably a bad sign, and you’re likely lacking the right product-market fit, customer validation, or something else. Yet VCs don’t grow themselves. It’s rare to find a VC in 24 cities, 13 states, and 2 countries, which is gener8tor’s footprint. We’re trying to push the envelope on what it means to be a VC and we think for an industry that prides itself on originality that we can infuse a lot more creative thought into what that means.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

I believe in allowing people the right balance of autonomy and support. As a manager, it’s important to give employees the appropriate autonomy that they seek to let them command ownership and have agency around what they do, and to have ownership for their outcomes and deliverables. At the same time, it’s important to recognize if, when, and where they need support such as financial resources, human capital, or tools to perform their job better.

The challenge we face as a manager is to balance these appropriately so that you’re not suffocating someone from having the autonomy that they desire while also fully supporting them at the right level of staging and pacing.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Entrepreneurs should focus on objective outcomes as a way to stand out and build trust. As a company that invests in startups, when a founder provides a five-paragraph essay but doesn’t include a single number or dollar figure, that signals we’re not seeing the full picture. The advice I have is to focus on objective numbers and include metrics front and center. Objective numbers are things that can’t easily be manipulated such as customers, revenue, and growth.

Can you help articulate why doing that is essential today?

Objective numbers aren’t just needed in pitch presentations; they’re also essential for holding each other accountable. As an industry, we need to change and do better with who we invest in and the biases that we have. At gener8tor, we publish all of our portfolio diversity statistics. Anyone can visit gener8tor.com/statistics to see our full investment portfolio as it relates to race, gender, ethnicity, veterans status, immigration status, and a host of other demographics that we obtain.

We encourage other venture capitalists to have the same degree of transparency and encourage limited partners (investors that invest in VC funds) to demand this type of transparency. We also hope that entrepreneurs increasingly call for it as they’re evaluating who they want to take investment dollars from.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur; you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

The highs and lows for entrepreneurs are best described as a roller coaster ride or treadmill! The reality is you shoot for the mountaintop but as soon as you think you’re at the top, either it gets higher because your perception was off, or you see another mountain in the distance that you’re now motivated to climb.

Another way to look at entrepreneurship is to think of it like the first time you get on a treadmill. You’re winded and gassed because you’re out of shape, but the reality is the treadmill is the business. It keeps gaining speed as your business does better, you become more successful, you gain more resources and you build a team and entrepreneurs must work hard to maintain momentum. Then you experience the highs and lows: You can go from selling your biggest deal ever or getting a new investor to dealing with an issue stemming from a customer, team member, or startup you invested in. What is even harder for me personally is that the highs don’t always reach the same emotional magnitude that the lows do. I take time to celebrate even the smallest wins so that I’m not pulled down by negative things that bubble up.

Every entrepreneur will be challenged to determine how to weigh a win and a loss or a positive and a negative. The challenge is to maintain or improve your stamina. Be self-aware and try to overcompensate so that you have the dopamine with those highs to persist and to smooth the lows.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

The best highs we have at gener8tor are when an entrepreneur has a breakthrough moment. This manifests itself when a company raises a Series B round of financing, lands a really great customer or if they’re a consumer-based company, rides a great wave of customer acquisition.

I always go back to our ethos which is putting the entrepreneur front and center of everything we do. Celebrating the wins our entrepreneurs achieve, whether it’s fundraising, traction, or revenue, but also witnessing entrepreneurs gener8tor has invested in a go from a napkin idea with one or two founders to growing to millions of dollars in revenue and dozens of employees.

One of my favorite success stories is Bright Cellars, a subscription-based wine club that sells wine based on a customer’s taste algorithm. They came to gener8tor with two founders and their first employee. After finishing the program, they raised $2 million, relocated their headquarters to Milwaukee, and grew to a team of 50 full-time employees. Witnessing and being a part of Bright Cellars’ successful journey is an uplifting experience.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

I think for any entrepreneur a lot boils down to the team and people dynamics. Whether it’s a disagreement internally or perhaps, in our case, an investor disagreement with a founder.

In my eyes, the biggest compliment gener8tor can give someone is investing $100,000 in them as a person and entrepreneur. It can be difficult at times to recognize that we don’t have all the answers, we’re not always right and we don’t always see eye-to-eye on every personal or business matter an entrepreneur encounters. For me, it’s keeping the perspective that we invested in this individual because we believe they have the right mindset, skillset, capability, and aptitude to grow their business. We need to trust in their ability and make sure they feel supported and yet maintain full agency over the decisions they’re making.

For us as a company, we have more than 70 full-time employees and the law of large numbers makes it inevitable for people to be on the move. Dealing with personnel issues and making sure we have the best team possible while we continue to scale is something that weighs heavily on my mind, as I’m sure it does for any entrepreneur. As we grow, I spend time thinking about how we continue to foster a great culture that attracts and retains the best talent. As an entrepreneur, you don’t set out to recruit people, you set out to build a great product and a great company. I reconcile this with in order for us to have the best company, the best accelerator program, and the best OnRamp Conference Series, we need to recruit the best people to our team to execute on those programs.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

Volume-Based Approach. Take a volume-based approach when it comes to rejection. Oftentimes, I see entrepreneurs self-defeat and use the thought of hearing a “no” from a customer or investor as justification for not even trying to take the shot. The reality is whether you’re talking to customers or investors, the number one response you’ll hear is most likely a rejection. That isn’t saying you’re insufficient or your product is bad; it’s realizing this might not be a good fit for this particular customer or investor.

Being self-aware of the reality and pushing against the headwinds is paramount for an entrepreneur to be successful. Entrepreneurs should optimize for as many shots on goal as possible. With our gener8tor programs, we aim to schedule 100 unique investor pitches for each of our startup cohorts. We schedule so many one-on-one meetings with investors because we never know who is going to say yes to a given startup. If it takes a startup 100 pitches to get a “yes” then I’m glad we scheduled 100 pitches instead of 99.

A mantra I like to use for early-stage entrepreneurs is, “You have more time than money. So, good use of your time is taking these shots on goal.”

Strong Brain Trust. Who is your person? Who can you speak candidly with and unfiltered with? This can be a person inside or outside your teams such as a family member, spouse, executive coach, co-founder, or someone else that you consider a close partner. Think of this person as someone with who you can speak candidly and on an unfiltered basis. For entrepreneurs, it’s critical to have a strong brain trust. Someone with who you can share your thoughts, frustrations, and wins as well as get critical feedback back is important for you and your business.

It’s a Long Journey. Being an entrepreneur is a long journey that has highs and lows. Don’t let one decision or inflection point determine the long-term outcome. It’s important to keep the business and your journey in perspective. A good motif I heard on this once was whenever things are going really well or really poorly, pull up Google Earth and zoom into your GPS coordinates. From there zoom out slowly to your city, then your state, country, and the whole world — the pin of your location becomes smaller. This puts into perspective how insignificant any one little action or activity is.

It’s a humbling experience that helps you realize that in the grand scheme of things, as long as your trajectory is positive and to the right, and you’re experiencing more highs than you are lows, that you’re achieving the net positive that you’re seeking.

Celebrate the Small Wins! In my personal experience, I find that the magnitude of bad news is greater than the magnitude of good news. This is why it’s important to celebrate even the smallest victories. Take time to send a gift to a team member because they did something above and beyond, go out to dinner with your family to celebrate a new deal, or take an extra day off or vacation because you deserve a pat on the back for that new investment you helped the company land. I find that being able to celebrate the little things keeps my head on straight. It’s also warranted and well-deserved when you’re working hard.

Be self-aware. Know what your core competencies are and have the self-awareness to realize that when you encounter uncertainties or turbulence, you’ll tend to revert back to your comfort zone. Oftentimes, when founders experience this, they go back to working on the product when they probably should be doing the exact opposite, which is talking to customers, selling, living with their customers, and getting feedback on the product.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

I see resilience as having a strong vision about what you’re doing while also having the ability to bend and pivot as needed.

As an entrepreneur, we control our destiny in the sense that we decide and prioritize our day-to-day, whether that’s talking to customers or investors or spending time building the product. While all entrepreneurs should have a long-term vision for the company, you should remain flexible and adapt the business based on market conditions, what customers are telling you and what you’re hearing from investors. I see this as the bimodal challenge of being an entrepreneur — knowing when to pivot and when to stay the course. It’s one of the most challenging tasks an entrepreneur faces.

In the gener8tor program, we call it ‘mentor whiplash’ when you have five people telling you one thing and five people telling you the exact opposite. Recognize that no single set of feedback is infallible. At the end of the day, an entrepreneur needs the resilience to triangulate all the feedback and set the course that’s best for them and their company.

As for how to cope during these challenging times, I think entrepreneurs should focus on the core deliverable and goals and how to meet or exceed those expectations. For gener8tor, the silver lining has been that we can serve even more entrepreneurs (our customers) in a virtual environment and connect them with even more corporations, customers, and investors.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

In every entrepreneur’s journey there comes a time when you question how you’ll make payroll, especially in those early days. We hope that we’ll never encounter this moment, but I think in many respects it’s a rite of passage for an entrepreneur. For us, it was in our second or third year, where certain projections didn’t come to fruition as we anticipated. This forced us to rise to the occasion and think more creatively about what our products are and the types of customers we could sell to. Ultimately, it’s made us a stronger company.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

I try to maintain an even-keeled personality and not get too excited or down about any one particular thing. The one exception is when it comes to startups we invest in; I’m always willing to believe every idea is a great idea.

As a leader, it’s important to always be focused on the vision of the company and not become overly emotional about any one decision. If you can keep the vision and your customers’ well-being front and center to all decisions, then you’re likely heading down the right path. For me, I take a holistic approach to stay even levelheaded and positive.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

“Excellence is more fun than mediocrity.” — Leonard Berry

I heard this quote shared by a high school principal at a graduation ceremony. It resonated with me because of how well it translates to what we do at gener8tor. I truly believe the more we focus on doing the small things well, improving the quality of outcomes, delighting our customers, and delivering outcomes above expectations, the better it is for everyone.

As our company grows and we gain more success, the more fun it gets. In the end, if gener8tor reaches its founding goal of creating a more efficient mechanism to help entrepreneurs succeed and we continue to evolve, then the whole journey will be worth it.

My advice for entrepreneurs is to keep the treadmill analogy — as you grow your business, you’ll need to build up your stamina. If you can keep up as the treadmill gains speed, and experience all of the highs and lows of entrepreneurship without getting tripped up, then you’ll ultimately be successful.

How can our readers further follow you online?

LinkedIn Troy Vosseller

Twitter @troyvosseller

gener8tor.com

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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