Every Founder Is Additive to the Wave

Women in Business is a standing Bellwether series about women who build things, and the people clearing the road for them. Each piece starts with a long conversation and gets written down early. It opens with a woman who spent four years deciding which Iowa startups got public venture money, and who is now putting the region’s best founders on one stage.

I.

The first meeting was held at West End Architectural Salvage.

Kaylee gathered what she calls “a ragtag group of volunteers.” Some of them drove in from around the state for that one meeting. She had lined up organizers from startup weeks in Reno, Colorado and Minneapolis, and asked Andy Stoll of the Kauffman Foundation to moderate the panel. She thinks it was 2024.

The meeting ran two hours. In the first hour, the panelists explained what it had taken to stand up a startup week in their own cities, and the room asked them anything. How much will this cost? What are the big barriers to buy-in? How do we know people will buy a ticket?

“There were no dumb questions,” she says. “We set the tone.”

In the second hour, people wrote on giant sheets of paper: ideas for tracks, and the gaps they saw in the ecosystem.

Jon Lensing was in the room. His company, OpenLoop, is one of the few unicorns to come out of Des Moines. He was fairly critical of the idea, and his question was simple. Why is Iowa a good place to build a company, when there are so many reasons to go to the coast?

Kaylee remembers the moment warmly. His objection “led to an incredible discussion,” she says, and it gave the event part of its purpose: “to expose the blind spots and to have a dialogue around what can this event do to address those objections.”

OpenLoop is now a major sponsor of Iowa Startup Week.

II.

It took a few years to get the thing on its feet. Iowa Startup Week is now a 501(c)(3) nonprofit. Kaylee leads it with Safiya Lee-Evans, Tej Dhawan and Diana Wright, and volunteers do the rest. Several people from that first meeting now sit on the organizing team or the board.

This is its first year. It runs September 28 through October 1.

The team was aiming for 200 tickets. Kaylee’s personal goal was 300.

“Everyone laughed at me,” she says.

With the week about to begin, they have sold more than 350 tickets, and more keep coming in. They raised a quarter of a million dollars to put it on.

“The market tells you if you have product-market fit,” she says. “And the market is telling us they want this kind of convening.”

Early on, she pitched Iowa Startup Week to the leadership team at Holmes Murphy, which also runs a program called Broker Tech Ventures. She had pitched them three years in a row for a smaller event she produced through the venture fund. Three years in a row they said no. It was too small, and the scope was never quite right.

This time the vision was bigger and bolder. They said yes, and became the event’s first large sponsor, at the silver level.

“I remember leaving Holmes Murphy and I thought to myself, this is really happening.”

At that point there were no other big backers. “You always remember your early believers,” she says.

Then all five John Pappajohn Entrepreneurial Centers asked Iowa Startup Week to host their 30-year anniversary. As far as she knows, the five have not been in the same room since John Pappajohn died. “It feels huge,” she says, “because of the impact JPECs have had on entrepreneurship and the people who have dreams to innovate.”

Then they booked Hoyt Sherman Place.

“It is the kind of place that reflects back to the attendees the grandeur of the vision that these innovators have for what the world can look like.”

III.

The week ends with Best of the Midwest, a pitch competition in bioscience, advanced manufacturing and software.

More than 200 companies applied from 13 Midwestern states. Thirty semifinalists pitch in Des Moines on September 30 in front of more than 25 venture firms. Six go on to pitch the next night at Hoyt Sherman, a historic hall that seats 1,200.

“We kind of need to fill it,” she says.

The rest of the week is built for four groups.

Founders from all 13 states. Many are in the competition. Many aren’t, and are coming for the people and for more than 80 speakers and three keynotes.

Universities. All three of Iowa’s regent universities are sponsors. Each is sending people from its innovation, technology transfer and patent offices to show founders how a university can help them commercialize.

Investors from across the region. “We’re so centrally located,” she says. “It actually is not a hard ask.” Firms are coming from Wisconsin, Kansas City and Nebraska, along with Lewis & Clark and others.

Ecosystem builders, the people whose job is to grow the economy through entrepreneurship: the Greater Des Moines Partnership, the Iowa Economic Development Authority, Polk County. One panel, Unconventional Champions for Entrepreneurship, features organizations you wouldn’t expect to champion people who build something new.

IV.

The pushback from that first meeting is still the main one. Why would anyone build a company in Iowa?

For women, the numbers are harder still. Iowa ranks 47th in the country for women-owned small businesses.

She put it to me directly. “I don’t know if you feel this way, Bonnie,” she says, “but when I look at the Des Moines ecosystem in my own network, it’s like my reality of Iowa doesn’t seem to reflect what the statistics say.”

She sees women business owners all around her. “I admire and deeply respect” them, she says. “They have accomplished incredible things.”

What is missing is critical mass. Other ecosystems have a density of people trying that Iowa hasn’t reached yet.

The fix is more people trying, knowing that most of them will fail.

“We know that 95% of startups fail,” she says, “but it is in the effort. It is in the attempt that you actually move the needle of innovation.”

Then she offers the image this series is built on.

“Each droplet, each founder is additive to the wave, regardless of if they make the very crest of that wave and touch a cloud.”

V.

What Iowa lacks in density, it makes up in access.

“Iowa is the kind of place where we have this underdog mentality, whether or not it’s accurate, kind of doesn’t matter,” she says. “We support one another.”

Her proof is concrete. If you want coffee with the CEO of Principal Financial, you know someone who knows someone who can make it happen.

“This is the kind of place where if you dream it, you can build it.”

She counts herself in that sentence. She had a dream for Iowa Startup Week, and the quarter of a million dollars came after it.

She is just as direct about where Iowa has an edge. She calls it an unfair advantage in fintech, insurtech, ag tech, med tech, biomanufacturing and biostimulants. These are highly technical fields, and the state’s three universities keep producing innovations in them. “They blow me away,” she says. “Truly blow me away.”

Then there is AI.

“There’s just never been a better time. Entrepreneurship has never been more accessible to the masses than it is right now. And I don’t want to see Iowa letting this moment pass them by.”

She wants the state to “reach out and grab their part of the swell.”

The mission of the week is a short list of questions. How do you start? How do you grow? How do you exit, if that’s what you want? How do you know you’re on the right track? Who can help you?

“But like all events,” she says, “you get out what you put in.”

VI.

Kaylee graduated from the University of Iowa with a degree in English. Her first job was an internship.

The company was VolunteerLocal, a scheduling platform where people could sign themselves up for shifts at events they cared about. She was its first paid employee. The developer told her the grant money would run out in about a month. If she wanted to stay, she could try selling the product. Maybe subscription revenue could keep her on.

She sold enough to bring herself on full-time.

Then she sold enough to hire the second full-time employee. The developer made her his co-founder. She opened an office in Chicago and moved to Raleigh to build the company’s East Coast business in the Research Triangle. She spent nearly a decade there, and eventually became president.

“I got to spend nearly a decade sort of playing and learning,” she says. “And the stakes were high, right? Because this is a real company with real customers and real employees.”

She doesn’t pretend it was easy. There were some really, really hard parts.

“But all of it is a gift.”

Then she joined Roboflow, a Des Moines computer-vision company backed by Y Combinator. She was employee number five and led customer development. She was there when the company closed a $20 million Series A.

“That was when the light bulb went off for me,” she says. Why didn’t I raise venture capital for my first startup?

So when she was offered the chance to build a publicly backed fund designed to invest directly in Iowa startups, she took it. For four years she was investment director of the Iowa Venture Capital Co-Investment Fund, a $30 million fund that invests at seed and Series A. For those four years, she was one of the people deciding which Iowa startups got public venture money. She stepped away in July.

She calls it the three legs of the stool. She bootstrapped a software company, helped build a venture-backed one, and has been a venture investor.

“I think that uniquely positions me to be the leader of Iowa Startup Week.”

VII.

I asked her why she does this work. Her answer had nothing to do with strategy.

“When I look back on my career, I feel like I was given so many opportunities to do a thing that is really hard to do,” she says, “and that not a lot of people get the opportunity to try or even give themselves the opportunity to try.”

She says the ecosystem coached her, held her up, celebrated her, reminded her, and at times ground her down.

“That’s what great mentors do.”

Iowa Startup Week is how she gives that back.

“I want to give that gift to as many people who are willing to receive it.”

Then she named who she most wants to reach.

“I’m particularly passionate about seeing women innovators step into, you know, commercial, marketable ideas. And so a big part of the reason why I’m doing this work is to try and expose more people who otherwise maybe wouldn’t consider themselves to be entrepreneurial.”

She means entrepreneurship as a career path, open to people who have never pictured themselves in it.

I told her about an idea I’ve been carrying: grant funding, and an angel club for women founders in the Midwest. In a state that ranks 47th, and a country where about 2% of venture dollars go to teams made up only of women, the gap is as much about who gets the first check as about who tries.

She said she’d take me up on it. We’re getting coffee in October.

Will she take any time off after the event first?

“To be honest with you, not really.”