16 Lessons From 6 Startups
Since 1992, I’ve either launched or been involved/invested in six startups.
- Computer Reseller (1992)
- Wireless Thin Client Tablet (1997)
- Application Service Provider (pre- “cloud”) (1999)
- Music Streaming Service (pre- Apple and Spotify) (2005)
- Music Discovery Platform (2015)
- AI Platform (2019)
All along the way, there were peaks and valleys with each venture. It’s very true that entrepreneurship is tough business. It’s innovation meets common sense meets hustle. Even now, 27 years later I’m still learning. I’ve built a Founder’s Toolkit for a more practical approach for founders.
So, for my sake — for my kids’ sake and for posterity I thought I would document some important lessons. This is not an exhaustive list, but ones that were hammered into my brain several times through trial and error.
16. A great product will not get you to the promised land on its own merit. It’s essential, but about 30% of the equation.
15. Everything takes 3–4 times longer than you think it will. Planning and strategizing a big win is a necessary exercise, but there are no shortcuts.
14. Know your business. Pushing a product or service that competes with other products or services requires you to be an expert — period.
13. Know the numbers. Revenue is important. Costs are important. Profits are especially important. If you are working on razor-thin margins and trying to grow, you are fighting a losing battle.
12. Understand the adoption curve.
11. Don’t ignore anything out of fear or ignorance. How does your product stack up against the number one in your space? Face everything, I mean everything — head on. (Especially uncle sam).
10. How does this scale? Always be asking yourself (and the team if you have one) — how will it scale? Will costs outweigh profits if we go 10x?
9. Know when and how to raise funds. This one is especially tricky. There are many ways to accomplish capitalization and it’s a different game in every industry.
8. Does location and market matter for the product or service? Are you trying to sell sand in the desert?
7. Pay attention to detail and traction. Any little change in your product can produce a wildly different response from customers.
6. Customers. There are good ones and bad ones. Know the difference as soon as possible.
5. Know when to get hyper-focused and when to take a break. A day off golfing could produce a very important insight or revelation.
4. Find believers. People will either believe in what you are doing or doubt it. Find the believers and keep them close. Hire them if you can.
3. As Kenny Rogers sings — know when to hold em — know when to fold em. This is very difficult since most entrepreneurs don’t want to quit. There might come a time to fold up the tents. Did you learn a lot and have fun but didn’t make any money? Cool. Apply it to the next move.
2. Be humble and listen — a lot. You are the expert in your venture and that may cause you to talk a lot. You will have to listen and learn as much about your customers, product and space as humanly possible.
- Sell, sell, sell. Figure out how to sell as much as possible to your good customers. One of my mentors said early on, “expenses follow revenue and revenue solves a lot of problems.” This could be the golden rule — I don’t know.. there are so many.
