‘The startup founders I’ve talked to have struggled meaningfully with selling the company – I didn’t say.’

When he sold the company in Kyle weather It burned.

Growing up on 53rd and Viet streets, the Milwaukeean always remembers the hard-working demeanor of his neighbors. He moved to Compton following college as a cause. AmeriCorps Voluntary. Landed on Habitat for HumanityHe says he got his “dream job” as a station supervisor – until his mother called one day to ask for a favor.

Years ago, his mother turned his childhood bedroom into a workspace for her growing medical apparel company. Solaris, and struggling with managing day-to-day operations and rapid growth, urged Weatherly to take over the leadership of the company. Weatherly says what he thought would be a golden opportunity to bolster work experience soon “turned into a gold mine.” technical.lyThe company was bought by a European medical device giant in 2014 for an undisclosed amount.

“It was all 100% running the company, and I thought I was going to die at my desk,” Weatherly said. “Out of the blue, people wanted to buy our company at a steep price, I didn’t bother.”

In startup circles around Milwaukee, Frontdesk is often viewed as a unicorn for the city’s woodworking tech scene.

With his newfound financial freedom, Weatherly began planning his next move. He took a year off from corporate life and traveled the world, staying on Airbus and other short-term rentals as he traversed South America, Southeast Asia and Central America. He intends to start a business – or to retire altogether. But as the miles ticked by, Weatherly felt the urge to get back to work and make an impact.

When his friend comes, Jesse DePinto“What’s next for you?” He reached out to ask. The weather was still uncertain, but the experience of living abroad sparked interest in the short-term rental market. DePinto saw an opportunity to jump into the market.

The two founders started Front desk, an urban short-term rental company owned software solution that automates and scales operations. Within a few months, the company, which works with landlords to “maximize the value of vacant units,” was generating more than $40,000 a month, Weatherly reported.

Frontdesk has raised more than $21 million per Crunchbase, including a $4 million round completed earlier this year. While Weatherly wouldn’t disclose financial terms, he said he is aggressive in the short-term rental market.

In startup circles around Milwaukee, Frontdesk is often viewed as a unicorn for the city’s woodworking tech scene. Could it be the breakthrough that Milwaukee needs? Ever the humble leader, Weatherly won’t say it, but he thinks his departure could be a factor in moving the city’s startup ecosystem forward.

Technical.ly sat down with Kyle Weatherly for a wide-ranging interview to discuss his journey from home builder and volunteer to successfully transitioning to the front desk of one of Milwaukee’s most popular and successful startups. This interview has been condensed and edited for brevity.


Working for Habitat for Humanity was a dream job. You’ve returned to Madison, Wisconsin and enrolled in graduate school to become a station supervisor—and you’re called to work with your mother growing up. What made you switch gears?

I technically work full time, I go to school full time [pursuing nonprofit management], and worked on a capital fundraising campaign. I thought I would serve for a year and then go back to work. I fell in love with working at Habitat, but I also wanted to lead and had career ambitions. My goal was to run a Habitat somewhere in the world.

The funny thing is that my entrepreneurship at that time was to get out of my bedroom so my mom could start her business. When I finished my graduate studies, she always complained about me running the company and said, “Why aren’t you running the company?” She used to tell me. My interest was with Habitat, but it was an opportunity to present my resume. Do I go back to running a home or run a small company for two years? She had five employees. I went with option B. Obviously, it turned out to be the best decision of my life.

In the year In 2014, Solaris was acquired by the European Union for undisclosed terms. Can you tell me what influenced your career moving forward?

Long story short, my mom put me in a position where I had a lot of leadership when I was 26. I really liked working in a small business. As much as I would like to say that the end was “goodness”, I got a lot of satisfaction from the private sector by trying to be good at my job, suppliers, customers and employees well. I tried to apply the same ethos of trying to do right by others that you find in the nonprofit world.

The thing I came up with later is that one of the things I enjoy about Habitat and running a small company is that you can start at point A and see point B. Like planting a shed or building a roof, you can see progress. When we grow to 150 employees, not much. On a large scale, it was very difficult to improve things. It was much less clear to see the impact of my work.

I stayed until 2016 when we sold the company in 2014 [the acquiring company] They were great; Not a complaint. We sell for dollars, but I sell for financial freedom. Looking around, it was a good job but when you have the option to do the job and get more joy and satisfaction, it just wasn’t my cup of tea.

Struggling to leave the chapter?

Every startup founder I’ve talked to has struggled meaningfully with selling the company – I haven’t. At one point, Solaris was my only interest in life; It’s where my self-esteem and identity come from. If we have something good [report] When I get email updates at 7pm, wherever that lands, it literally makes me happy or sad. Everything was 100%, and I thought I was going to die on my desk. Out of the blue, people wanted to buy our company at a steep price, I didn’t bother. Part of it was growing on 53rd and Vliet, in a working class neighborhood. The idea that I could be financially secure at age 34 was… pretty much impossible. I never thought about selling Solaris until someone offered to buy it.

You’ve worked in leadership since you were a kid, but obviously, the exit gave you a lot of financial freedom — and options. Why did you choose startup?

When I leave, I ask, “Do I want to start a business, go back to business, or retire? I was a little nervous that I might want to retire. I worked a lot in Solaris and going through the sale was a very difficult process. We had structure. [the deal] On the way to the US headquarters in Milwaukee. The strengthening exercises were incredibly intense and I was burned out. “We would never regret taking a year off to travel,” I thought. I went out [Solaris], we got married, and my husband and I traveled the world for a year. After about three months it became clear to me that I wanted to work again. Then my business partner [DePinto] He asked me what I wanted to do next.

Frontdesk has become one of the city’s most successful startup stories. Why did you choose the startup path and how has being CEO been different from the experience of running Solaris?

It’s like night and day. To be honest, when I started running a company at the age of 26, you have a lot of vim and energy and want to learn everything. I may want to control more than I want to be controlled. But, even before we left, I was bullish on short-term housing; We used Airbnb a lot, and I became very knowledgeable about that place.

Today at Frontdesk, we’ve partnered with multi-family landlords to maximize their living space. We are able to take empty inventory and turn it into short term rentals in a safe, secure and reliable way. One of the smartest things we did [as a startup] – and I don’t want to sugarcoat it – I loaned the company money, and we made a fist. My wife was able to work in the company, and I worked for free. But it wasn’t until we made $40,000 in revenue [per month] As soon as we start raising money. It forces us to have a level of financial diligence and thoughtfulness.

It’s very easy for a startup to say, “I want to do A, and raise money to do that.” We [grew the business] With our current limitations. We depend on the cash flow, and then we can grow. Eventually, when we wanted to scale, it needed capital. If you can’t identify product market fit and best practices, I haven’t raised money. I’m not wired that way.

Make no mistake: Covid was incredibly difficult. We probably went out of business six or seven times. If it wasn’t for my enthusiasm to work, I might have given up. I don’t know if I would have been as strong as a leader without him by my side. Thankfully, we are seeing the other side.

According to Crunchbase, they’ve raised north of $21 million, including $4 million in their latest funding round earlier this year. What do you guys have next?

We are still in the market for a surprise. We think we can be the No. 1 or No. 2 urban short-term housing provider in the US. The market is growing in the future. We’re incredibly excited about the technology we’ve developed along the way and creating deeper relationships with customers. We are looking to sell our software, our PMS. [property management software]Currently for A [handful of operators in our space]. We think there is great potential. Our software has enhanced our growth and financial performance. It attracted other people in our niche to want to use it. We want to press that advantage, as well as other opportunities in short-term rentals and multi-family space.

What is your overall impression of the Milwaukee tech startup scene? Are we on the cusp of a unicorn?

I hope this doesn’t sound like “the grass is always greener…”, but I personally wish we could learn how to train and inspire more people to start a startup. I will say, the complaints we have about our program will not stop, I will say that when you find cases where other states and cities do not have those programs and still do. [thriving]. We don’t seem to have a culture these days of people who are willing to quit their jobs and start a very modest business at the level that requires a very active startup scene.

My advice to young founders is that if you want to get involved in startups, you can get to know everyone. [Milwaukee’s tech scene] in three months [networking] or email. I have never said no to a meeting. People here are extraordinarily approachable. I don’t know what the solution was, but almost every “tech city” with a good culture and lots of participants had a big outlet. You must have a unicorn; Then you suddenly have hundreds, if not thousands, of stock options or enough money to chase your dreams.

The training required to work at a startup is very different from corporate America. If I can swing the magic of a couple of priorities, we should be lucky with a few unicorn exits and we need a lot of people with passion, talent, and money for startups.

What do you think helped you become a successful entrepreneur?

Look, there are people who are true geniuses and great leaders. For me, my experience is 90% right place, right time. I went to graduate school with a lot of talented people and I was the only one who knew that I was given the opportunity to lead a company at the age of 26. My mother didn’t know either. Gold mine. My experience is good luck and good judgment, if I deserve any credit, I’m thinking in the long run. I was willing to go to Habitat for Humanity, I was willing to invest in graduate school, and I was willing to work with my mom—a very low-paying option at the time—and I was willing to reinvest in the company later. I’m good at delaying gratification.

But 90% of the time, it’s just good luck. Guy will be rich, he will invest.

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