As a starting point of the series, it only seemed fair to provide my own experience as a founder before I asked others to do the same, knowing this will be the least interesting of the series. I’ve tried to be as candid as possible in my recollection, although I’m keenly aware that time has a way of distorting early events. For the sake of consistency, I will use a similar Q&A format for this installment as the others.
Tell me about your background, how did you get started?
From a young age, I’ve always had a disposition toward being an entrepreneur. I remember various business ventures including car washes, selling used golf balls and beer (unlicensed) to country clubbers, creating a market for high-quality pens in elementary school, a barter system for Subway sandwiches in high school, and business ventures in college [that are] better not discussed. My businesses in adult life have been both legal and properly licensed. I come from a long line of entrepreneurs on both sides of the family, some more successful than others.Why Govtech?
My interest in urban planning started at an early age. I was a power user of SimCity in elementary school. I was incredibly lucky that my elementary school was a part of the national SimCity competition, where we were required to build a virtual city that met certain criteria, then build a physical model of the same city, and then present the model to professional engineers and planners. It was a formative experience early in life that provided exposure to both how cities operate and how technology can play a role in the development process.I went to college intent on becoming an engineer. In retrospect, given my general lack of interest for traditional schooling and extreme interest in social activities, I should have selected a less rigorous path. It turns out attending 10 percent of classes my first semester of college sealed my fate as a non-engineer. My awful judgment pursued; after spending a single semester in landscape architecture, I decided to find a major that suited my lack of interest in schooling: geography.
My good luck continued when I was able to cajole my geography professors to allow me to not attend class and simply submit papers and take tests. This allowed me to work full time as an urban planner at a consulting firm while finishing school, prior to spending time working at the city of Phoenix.
Each step in that process confirmed two things. First, the work of government is fundamentally important, both within and from the outside. Second, the opportunity to use modern technology to improve all facets of government was enormous.
Looking back, what’s the most important attribute for an early or first-time founder?
Naiveté and perseverance, hands down. You have to be naive enough to believe you can actually accomplish something that hasn’t been done before. Starting a company is [incredibly] hard. Getting to product market fit is [incredibly] hard. Hiring people is [incredibly] hard. Raising money is [incredibly] hard. Managing people and investors is [incredibly] hard. If your goal in life is to limit stress, don’t ever start a company. If you knew how hard everything was going to be, most people would never start a company. You have to be equal parts naive and equal parts insane. Which leads to the second attribute: perseverance. When you start a company, you typically don’t have the luxury to think about the future. It’s pure survival mode.Over the course of 10 years, you are bound to experience some of the highest highs and lowest lows. The only common attribute of successful founders is their ability to persevere through the lows and graciously accept the good luck of the highs.
What’s one thing you would do over?
That’s actually a really tough question because so many things in a startup are interrelated, so changing a single thing often creates a cascade effect across so many other things. With that said, I would have been more selective about hiring, particularly important positions. In the long run, it’s way more important to get the very best person for the job than it is to fill the job fast. Filling open roles fast caused a lot of headaches, both physically and culturally for us at different points.You’ve raised venture capital; talk about the experience. Would you do it again?
I think about this often, would I raise money for my next business. I think the answer of course is it depends on the needs of that specific business. I generally try to avoid absurd absolutes like, “I will never do this or I will always do this.” Those don’t work out well in the end. At the end of the day, there’s nothing more valuable than equity. Equity is the currency that startups run on. I think people forget sometimes that when you raise money, what you are really doing is selling a majority stake of your company. You are inviting other people into your home, and not temporarily — forever. That’s a big decision, and one that often gets lost when you’re discussing terms of valuation. Be thoughtful about who you invite in your home.If you were giving advice to a first-time founder, what would the advice be?
First, find a great co-founder. Nathan and I started the company (MySidewalk) having worked together before and deeply understood each other’s strengths. We trusted the other person to execute in their area of competence. Everything works better when you have a competent person by your side.Second, be willing to pay the price of success. Too many people confuse a statement like this with not sleeping, ignoring personal health, or not maintaining your personal relationships. If those things are out of balance, the company isn’t going to be successful anyway. What I mean by this is simply, are you willing to spend every working hour for the next 10 years solving this particular problem? No hedging it’s only this problem. For. Ten. Years.
If you were giving advice to a public-sector employee who’s trying to purchase and use modern Web software, what would it be?
In my experience, many public-sector folks have trouble articulating exactly what problem they are trying to solve, which results in a loose description of why they need a particular kind of software. A helpful tip might be to try writing a job description for what the software needs to do. If you were to hire a person to do this job, what would the skills and requirements be for the job? It also helps to quantify the value of software for management or procurement folks. Literally ask them, if we tried to hire a person with this set of skills and capabilities, what would it cost? In almost every case, it would cost far more than the software you are trying to purchase.What most concerns you about the broader govtech space?
For starters, I’m long-term bullish on govtech/urbantech. In the short and intermediate terms, I think there are a lot of things to be concerned about. The microeconomics of most companies in this space aren’t great. Cost of acquisition is high. Renewal rates are much lower than enterprise SaaS (Software as a Service). It’s not really SaaS because deployment takes people. Will those things get sorted out, I think so. To pretend they don’t exist today by pointing out one or two counter examples is a disservice to the space. It’s a hard space to scale in right now.Book recommendation for other govtech founders?
So many good books. It’s a great time to be alive for avid readers. Here are my favorites:- On Writing by Stephen King
- Competing Against Luck by Clayton Christensen
- Influence by Robert Cialdini
This interview was originally published by Better Planning.
