What We Learned After Our Exit(s)

Today we have two very-special guests: my current co-founders Chris and Nikki Ridenour. Before they were a married couple, they started in 2012 as co-founders of LISNR - an ultrasonic proximity platform. Chris as an engineer and CTO, Nikki as a designer. After working with a ton of major artists and hosting 30K+ user activations, they raised Series A with Progress ventures. Shortly thereafter they left the company in 2014. That lead to Chris founding Casamatic and going through both the Ocean and Brandery accelerators in Cincinnati - and later raising a seed round from Accelerant. After pivoting from b2c to b2b they decided to shut down the company and return the funds to the investors. Chris then joined me as CTO of Cladwell for 2 years, while Nikki went through the Uptech startup accelerator with her startup Farmbee. Chris later joined Nikki on Farmbee after they had their first child. Now - they are current co-founders with me in Boilerplate.legal.

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Here's what they learned:

1. Four first time founders and one founder who was CEO of another startup was probably not a recipe for success (link)
2. Early advisor shares are so easily wasted. (link)
3. You have no idea what your job role will entail - despite always having the title of CTO, I have shown people houses, run interviews, been a full-time audio editor, graphic designer, video producer and editor, competed in pitch competitions inside NFL stadiums, etc. (link)
4. Founders have to be in it together - having done this four times now, it’s obvious when the entire team is taking on challenges together versus seeing each other as skill sets to move things forward. (link)
5. No one understands your product or customer better than your leadership team after only 15 minutes. No matter how great the meeting was, don’t pivot your product on a dime. (link)
6. Find a mentor with a different skill set than you.  (link)
7. If you’re a minority founder, the company’s lawyer is there to represent what’s best for the company, not you. (link)
8. Think about yourself four years ago, would you make the same decisions then as you do today? If not, understand vesting is not to screw you over. (link)
9. Understand the legal stuff during the raise, or have a great lawyer who does. Things can change in the 11th hour and have huge impacts on the company, founders or both. (link)
10. Speed is important, but if you have any doubts at all about your lead investor, don’t move forward. (link)
11. Get all documents up front before joining an accelerator. Understand you probably won’t be able to negotiate (you have no power if you’re pre-revenue) but you probably want to pass on any secured notes up front. (link)
12. Take advantage of every benefit of the accelerator: a larger “team” to motivate you, mentors who will be less available after. Being an alumni has some benefits, but not as much. (link)
13. Demo Day is primarily a spectacle for the accelerator, not for you. People who raised post-demo day (including us at Casamatic) already had laid the groundwork prior to that. It may move the needle if you nail it, but raising money is usually about who worked hardest on fundraising. (link)
14. Be careful who you surround yourself with.  (link)
15. Months matter, years matter. But probably not weeks and definitely not days. Pushed off honeymoon at least three times for “important deadlines” and when we finally went, it still “felt like a bad time” but I had been driven to a point where I didn’t care and that just looked bad for me, the team, the “deadline”, etc. (link)
16. If your investor changes their board member to someone who doesn’t share your vision or isn’t providing value, don’t try to please them. This probably killed any chance we had at Casamatic. (link)
17. Don’t pivot to a sales-based company if no one on your founding team wants to do sales. You can’t hire out to find PMF and sales has a way of burning people out who don’t want to do it. Especially cold calls. (link)
18. Avoid selling to sole incorporators, as they demand the attention of a business but won’t pay more than a consumer. E.g. real estate agents, farmers. (link)
19. Understand your target B2B customers biggest perceived need. If you’re not providing it, you’re likely a distraction. Even if you can show them benefits in other areas of their business, if you’re not moving their one needle, they will smile and nod. (link)
20. Don’t linger. When something isn’t working, move on. Fail fast sounds so great, but when you’ve taken people’s money, put reputation on the line, it’s a different feeling. When you’ve lost belief and have no path forward, return the cash and hand the reins over. (link)
21. When inheriting an existing team, take ownership of them and don’t be afraid to suggest hard truths. (link)
22. Remove everything in the way of making big swings. Even if it hurts feelings or “worsens” the product. If your servers aren’t on fire 24/7 (in a consumer product) you probably don’t have it yet. (link)
23. Make sure everyone on the leadership team is interested in building a business. (link)
24. Make sure everyone on the leadership team is interested in building the SAME business. (link)
25. Avoid creating a culture of us vs. them between founders / employees. Give leaders ownership of their side of the business and make sure their teams are included. (link)
26. Talk to as many other founders as you can find the time for. Startups can be a lonely place, especially if your friends/family work in stable 9-5 jobs. When you’re part of the 90% who don’t make it big, you don’t want to feel like you suffered. (link)
27. Gut-check with yourself every few months to make sure you like the actual work. After over 8 years and plenty of 80+ hour weeks (and plenty of normal ones too), I still like early stage product development, etc. But if I didn’t, I would adjust out quickly. Again, 9/10 times the journey is the only thing you take away. (link)
28. Pro-tip: You will see your co-founders more than your spouse. Just make one of them your spouse. (link)
29. Venture may not be for you. (link)
30. Almost everything is a distraction until you have feedback. Build the most primitive version of your product you can and sell it as quickly as you can. Boilerplate went from idea to first customer in 90 days, not full time hours, no funding. (link)
31. Find people who will call you out when you’re distracted, stalling, procrastinating, wallowing, indecisive etc. Set up feedback systems that aren’t delayed. Involve other people often so you can course-correct and get help knowing when you’re in reality or fantasy. (link)
32. When you’re stuck, try to move the needle, just take action, “excellence is the next five minutes or nothing at all” - Tom Peters has gotten me through a lot of hesitation/stuck moments. (link)
33. I enjoy documenting milestones and decisions made, saving product screenshots, customer feedback (just in the workflow of day, this isn’t like a scrapbook project) and looking back on that stuff periodically. It lets me see the movement/progress instead of just feeling like everything is a continuous blur of time. (link)
34. Set expectations and don’t feel pressured to work on the same project if the passion isn’t there. At multiple times, I worked full-time so she could start a new company / vice versa. Expectations at home were also adjusted accordingly. (link)
35. When working together, don’t bring work home, even if you work from home. Create barriers and stick to them for the most part. Especially if you have other team members, you don’t want to come to a meeting pre-agreeing. (link)
36. Create the distinction between each other to teammates. When you’re talking to Chris you are NOT talking to Nikki, and vice versa. We don’t have a shared knowledge base or memory. This is something we’re still trying to do better. (link)
37. Even with both of us being founders, past founders, etc - it doesn’t make it easier when one of you has to solo-parent on a weekend because the other is catching up on work. Or feel like you haven’t had an adult conversation in two weeks. That will always suck, regardless of how much you understand / are in the weeds too. (link)
38. Plan family decisions around what works for your family, not your company. Hint: having a baby is never “good” for the company. (link)

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