Unseen Entrepreneurs

Why are some innovators so easily overlooked?

By Peter Zaballos

I want to tell you about a serial entrepreneur I know in the small town I used to live in.

When my wife and I moved the family to Wisconsin in 2001, the state was “trending” — its economy was fairly strong and it was attracting entrepreneurs who were finding like-minded folks interested in bringing new ideas to life away from the intensity of the coasts. (This changed during the recession, and Wisconsin, at least, hasn’t really recovered.)

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The region in general is one where there is not a lot of risk taking. For good reason — if you’re a farmer you control so little of what might make your season successful, you can’t count on abundance every year. Taking risks is hard, and being bold even harder. When I was a venture capitalist looking at investments in the Midwest and as an executive at a technology firm in the Midwest I ran into the same thing — a very complicated relationship with being bold.

That entrepreneur I know there, while born and bred in Wisconsin, seems to have the same high tolerance of risk that I do. And, like me, when they see a problem or opportunity they have a viable solution for, they can’t not do it — they simply just can’t let it go.

Let me give you an example. In our college town of about 14,000 residents — only about 8,000 are full-time residents (the rest are students living in rentals who generally leave over the summer) — a small farmer’s market in a parking lot of a hardware store on the edge of town brings a dozen or so produce, honey, and other vendors together with the people who want those things on Saturday mornings. People drive in, pick up what they need, chat with a vendor or two, maybe stop into the hardware store, and leave.

It totally works in terms of a marketplace, but it misses a bigger opportunity — creating a space that could bring the community together and foster business, cultural and social growth.

The entrepreneur I know was a founding board member of a downtown revitalization organization that was frequently asked by community members to bring the market downtown, where there are parks and greenspaces designed for public events and businesses that could use the added foot traffic. Multiple times the group reached out to the Saturday market — once going as far as scouting locations with them — but the Saturday market always ultimately declined to move downtown.

Everyone saw this as a problem with just one solution: get the Saturday market to move downtown. When the City Council asked the downtown group to try, once more, to establish a downtown market, the entrepreneur went outside of the box and proposed adding a second weekly market instead.

They were met with “Why do that, when we already have a farmer’s market?” and “Are you going to be able to get enough vendors or enough visitors and customers?” and “Isn’t it too late to start a market this year?” The entrepreneur didn’t know the answer to any of these questions, but they were willing to try anyway. So they proposed 1) a team of key stakeholders, including vendors from the Saturday market, to plan the market, and 2) that the new market be a pop-up, a proof of concept, to make people feel less anxious about the risk.

This is where their world and my technology startup world have a high degree of alignment. Starting a tech company is one long slog through “won’t big company X just kill you?” or “that’s not going to get to scale” — in both of our cases you create something by focusing on the very small number of reasons why it will succeed while ignoring the substantially larger number of reasons why it will fail.

The entrepreneur led a team through the process of researching the market, engaging key constituents such as city officials and understanding their concerns so they could be addressed, deciding what kind of market they wanted to be (Grower only? Arts and crafts? Dog-friendly? Live music? Food carts? More about the quantity of options or the quality of options?) and then, finally, deciding when and where it would happen. Subgroups focused on critical operations needed to make the market happen: working with the city streets division and the police to ensure public safety and needed infrastructure like trash pick up and caution cones; attracting vendors mid-season (to reduce perceived hurdles for risk-intolerant vendors, the entrepreneur had the key insight of waiving vendor fees for the first year); and getting the word out to the community, among others.

With clarity of vision and a well-thought-through plan, the team launched Whitewater City Market on July 21, 2015. The planned layout was for eight vendors: 17 showed up. By week five, 45 vendors were coming, and the community was showing up in droves.

The entrepreneur and their team worked furiously to keep up: collecting stats, taking surveys, meeting every week to assess what went well, what didn’t, and adjusting accordingly. And with clear consistent communication and a continuous process improvement approach — the market came to feature local craft beer and kombucha and moved from its initial location to one that provides more shade, among other improvements — the number of weekly vendors grew to 60 (after swelling to 90, a number unsustainable for the size of the town), and the visitor count routinely exceeded 1,000. 

This is significant in a city of 8,000 full-time residents. Imagine creating — out of thin air — a forum that brings more than 10% of a community together. Every week. 52 weeks a year. Because, by popular demand, the market runs year-round, moving inside a local library on Saturday mornings November through April where about 20 vendors offer eggs and kombucha and bread and winter vegetables and aquaponically grown greens and the like. The market is sustainable, generates income for vendors and its parent organization, and supports two part-time paid internships.

And there are numerous unseen benefits to the market. In recent years the community lost its local grocery store, so the need for locally produced food is even more critical. The market offers “incubator” spots free of charge to new vendors for up to three markets so they can test whether there’s a market for what they have. Because there are two markets in town — the other one continues to happily plug along — having two places to sell his produce helped at least one farmer stay in business and on their farm.

And the large number of customers make for fast innovation: the market’s honey vendor went from testing home-brewed kombucha with customers to bringing it to the market, launching Komboocho Brewing, selling it at multiple markets and finally commercially canning and bottling it and making it available in retail locations in less than two years.

The Whitewater City Market is also the only place I know where you can get your axe sharpened while enjoying a wood-fired pizza.

Truly a success story, and one of many I can tell you about this person. Before I introduce the entrepreneur, tell me — who did you imagine them to be? 

If you pictured a man, you wouldn’t be alone. The image most people tend to have when you say “entrepreneur” is generally about mostly men building high technology companies. Lots of growth. Computer science nerds. Engineering chops. 

What if I told you that entrepreneur was my wife, Kristine?

I wrote earlier about the painful lessons Kristine and I learned when we decided she would leave her career to care for our children and I would focus on my career. It did my career well — I’ve spent it entirely in high growth technology startups and as a venture capitalist. Hers, not so much. So, over the years she’s thrown her excess capacity into side projects that combine her strategic ability to see viable solutions to an unmet need and and her dogged focus on process and communication to actually get the job done.

The more I witnessed the success and trajectory of the Whitewater City Market, the more it became apparent that I was, in fact, married to an incredible entrepreneur. Starting a city market was exactly about seeing a need no one else has seen — or, if they had the idea, was unwilling or unable to see through to fruition. Because, in life as as in tech startups — ideas are cheap; it’s execution that matters. 

And the skill and insight to do this is the same whether you run a tech startup or a nonprofit. The need to deeply believe in the value of your solution in the face of — best case, aggressive indifference, but more often disbelief or opposition — is exactly the same. And the need for funding, to be constantly fundraising and making due with what your financing will support — also exactly the same. 

Don’t believe me? Let’s see what key challenges both for-profit and nonprofit leaders face:

  • Identifying a truly unmet need. That’s easy to say. Maybe it’s better framed as “seeing the potential for a solution when no one else does.” It’s the same whether you are building a software-defined anything or bringing a community together.
  • Assembling a leadership team. Whether you’re a venture-backed startup or a community market manager, finding competent leaders who can scale what you’re doing is hard. And essential. 
  • Leading. Leading with a capital “L” is essential to any business breaking new ground. This is so much more than leading employees and volunteers. It’s about orchestrating buy-in from all the people and entities that have an influence on your idea. Investors, partners, government entities, neighbors, and even competitors — they all need to see the potential and follow.
  • Communicating a vision. This is inextricably linked to leading. But in a nonprofit you are leading people whose compensation is not financial. Communicating a vision to inspire volunteers is sure a lot harder than doing it for folks you are paying to listen to you.
  • Orchestrating change. I mentioned before, in both for-profit and nonprofit startups the biggest execution challenge a CEO will face is orchestrating the massive change this new opportunity is going to require. It requires focusing the one reason you will succeed and ignoring the tens or hundreds of reasons why you might fail. 
  • Persisting despite setbacks. Another key quality of leading is pushing yourself and your team over the hurdles and regrouping and persisting when you hit a wall — and you will. Managing setbacks and outright failure is one of the most difficult and most vital aspects of leadership. 

It’s pretty much the same challenges — the difference is in how we reward success (or not). But despite the similarities, I have seen the bias against non-profit street cred first-hand when my wife and I go someplace and meet people, frequently other folks from the tech industry. When they ask what I do and I explain, there’s this instant acceptance and validation. And all I usually say is something like “I ran marketing at a cloud computing company.” And truly, all my companies have ever done is solve a fairly technical problem that, unless you’re in DevOps or are a CTO, you won’t understand or appreciate. But I get instant credibility and interest.

When Kristine explains what she does, the conversation path is short and awkward, and she is generally received with what amounts to “well isn’t that nice, you’re helping people.” I have seen the eyes glaze over, and I have rarely heard anyone ask a follow-up question. It really annoys me, because that rigid mindset is the kind of mindset that prevents seeing an incredibly successful serial entrepreneur at the top of her game.

I say “serial” entrepreneur, because the market is just one of the side gigs she manages on top of her day job in marketing and communications at the university in town. She’s not unlike Marc Beniof, who saw the potential for software-as-a-service and faced a full decade of “smarter” people telling him his idea would never work. (That idea was SalesForce.com.) Originally I’d compared her to Elon Musk, who started and runs multiple companies, but but both my wife and my daughter pointed out that he is rather creepy in terms of his relationships with women. 

What’s the tie-in with Beniof and Musk? In the same way people wonder how Elon Musk can run three companies at once, the people in our community (and I) wonder how Kristine can run all three of the businesses she is the founder and CEO of (more on the other two in another blog post) in addition to her day job at UW-Whitewater. She does it because she can’t not do it and she puts in the hours to make it happen. Just like all the entrepreneurs I know.

So why am I writing this? It’s hard not to acknowledge that this is most certainly a love letter to my wife. But it’s also a letter of admiration to an inspirational entrepreneur from a guy who spent 30+ years building technology startups and lamenting that people starting and running “nonprofit” businesses are not seen as peers to people running for-profit businesses. And when I say “people” — I really mean women as well as people from diverse backgrounds.

Kristine isn’t just “behaving entrepreneurially” but is in fact a kick-ass serial entrepreneur. Maybe you have one in your community. You should tell them that.

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