Dear Founders-
1. Identify an Annoying Problem
Startups are born out of frustration. Find something broken, inefficient, or painful—something that people quietly tolerate but shouldn’t have to.
For me, that was parking stalls.
2. Imagine a Solution
Picture a better world where the problem doesn’t exist. Your imagined solution doesn’t have to be technically possible yet—it just needs to feel right. For me, it was a 35 slide pdf that walked through how an algorithm for designing high density buildings might work.
3. Sell the Dream (Before You Build It)
Pitch the vision. Talk to potential customers. Try to get someone to pay—even if the product doesn’t exist yet. This validates demand and sharpens your focus. For me, this was a 5 minute pitch to the man I worked for. His reaction to the 35 page deck told me all that I needed to know: he would pay for that product if it existed.
4. Partner with an Engineer
Once you’ve proven there’s a real need, bring in technical talent to help bring your idea to life. Choose someone who believes in the mission, not just the code. For me, that was my close friend Ryan Griege, who was the only software engineer I knew in 2016. The mission at the time was whatever we could build and ship together.
5. Build Just Enough to Make a Real Sale
Your first version doesn’t need to scale. It just needs to work for one real customer. Use that sale to prove your solution isn’t just theory. For me, this happened in October 2017, about 3 weeks after I started marketing “Residential Engine”.
6. Tell the World You Made a Sale
Social proof is gold. Let the world know someone trusted you enough to pay. It builds momentum and attracts early believers. For me, this idea never came to fruition in my head. I was more concerned with making the product better between 2017 and 2020 that we never really talked this bit up. Dont do what we did here.
7. Raise Seed Capital (Sell ~15%)
With traction in hand, trade equity for fuel. Use your first investment to extend your runway and hire the right people. For us, this came in the form of Jesse and Gregg from Parkway. They stabilized the long term vision by anchoring us in commodity real estate–its what they invested in.
Our Lawyer, Andy Smetana, reminded me that in this stage you might be as likely to find a grant (Non dilutive investment) to help fund you. This is a great option.
8. Hire More Engineers
Speed is leverage. Expand your engineering team to build faster, fix faster, and outpace competitors before they wake up. For us, this meant finding exceptional talent that can think trigonemetrically, technically, and deeply. Our goal is to generate IBC compliant buildings in milliseconds.
9. Find a Real Sales Closer
You’re good—but there’s someone better. Bring in a professional seller who can take your product to more people than you could ever reach alone. For us this came in the form of Jack Joers. An architect/developer mindset from where he came from and where he was going made him and I fast friends, and for the first time I didn’t feel the need to be in every sales discussion. This saved my mental health dearly.
10. Partner with a People Person
Culture matters. Hire someone who sees people—not just headcount—and can build the team spirit that will carry you through chaos. For us this came in the form of Alexine Gordon-Stewart. I am not a super cuddly, lovable leader. In fact, I sit very far on the normal curve of abrasiveness. This is both my superpower but also my kryptonite. In the same way that a seed investment stabilizes vision, a Chief of Staff for me stabilized culture enough for me to grow.
11. Blow Through $1M in ARR in Your Niche
This is your first real milestone. Dominate your beachhead market. Get sticky, stay lean, and learn everything you can about your customer. For us, we absolutely owned configurators high density housing, become known for it, and continue to dominate this niche today.
12. Raise Series A (Sell Another ~15%)
Now it’s time to scale. Take capital to grow beyond your niche. Expand into adjacent markets and multiply your wins. For us this meant finding a market outside of high density housing that in and of itself could scale to >$1M in ARR. To get our feet wet we went into industrial (this was in the middle of the COVID boom) and partnered with Prologis on how to deploy warehouse logic at scale. This will be a billion dollar company, so we needed to find even more markets to sell configurators into…
These new niche markets for us today are retail, office, industrial, datacenters, civil engineering, and urban planning.
13. Design the Corporation
You’re not just a founder now—you’re building an organization. Codify what worked. Build playbooks, processes, and principles that others can execute.
For us this looked like a lot of failure. There were many corporate structures that I wanted to get into, but often sales, board meetings, or product releases got in the way. There were lots of different management meetings that, to me, always seemed to work at, like, 30% effectiveness compared to taking a dictatorial approach. I learned a lot in these meetings. My entire goal now is to eliminate 100% of meetings. If a meeting exists, likely it is a sign of a lack of process, or responsibility being squarely on someones shoulders.
14. Partner with a Growth Executive
As complexity increases, so does mental load. Hire someone who lives and breathes growth—who can scale what you’ve started and boost team energy. Tactics of go to market teams at scale need to be managed, tweaked, improved–in the same way that you, dear founder reading this, did it in the early days. Offload your thinking to others with more information than you. For us this came in the form of Laura Paciano, who had gone through two IPO level cultures at Procore and Sonos.
15. Hit More Revenue Milestones
Double. Then double again. Numbers are the scoreboard. Use them to sharpen your focus, rally your team, and signal to the market that you’re for real. For us, this is literally anything. First sale of retail? go nuts. The time we then closed Home Depot? Go to Home depot and take a selfie. Celebrate any molehill and make it a mountain. Momentum is your only friend.
16. Bring on a CFO
You need someone who speaks capital fluently. A strong CFO increases valuation, manages risk, and helps you build a business that lasts. For us, we really struggled to find a CFO. I was searching for what felt like years. Running the Series A process without any kind of CFO meant that I was the financial analyst, budget designer, deck maker, meeting scheduler. It was a disaster. Keeping your bank balance above zero is your core job as CEO. A CFO takes the cognitive and stress load for a bit. Now we Have Robyne Gaurdreau, our first CFO, and she keeps the process organized.
17. Complete the First Iteration of the Corporation
You’ve transformed the dream into an engine of value. Your company now stands on faith, honor, and discipline—ready to do it again, only better.