I picked up the book “Founders at work” on the airport bookstore while I was traveling from Bangalore to Toronto and I’m glad I did. The book is a compilation of interviews between Jessica Livingston and the founders from many of the 90s-era tech startups. Reading the interviews, you feel as though you’re sitting right beside the participants. It’s really riveting and I’ve compiled a few of my learnings.

Learnings about founders

• A lot of the founders understand each other fundamentally.
• It seems like when cofounders have a strong bond or understand and acknowledge each others strength’s and weaknesses, they’re able to support each other through tough times. A lot of the interviewees also seemed aware of their shortcomings and the need to partner up with someone who fills those weaknesses.
• Many of the founders had experience running businesses in the past.
• Founders had a great curiosity.
• Founders persevered through tough times.

Other Learnings

• Have the strength to follow your gut.
• It’s too difficult to radically change customer behavior.
• Make sure every year there’s an accomplishment you can point at.
• Simplicity is good.
• Giving seed investors “right to refusal” sucks because they can block subsequent funding rounds.
• Enterprise deals take about a yr.
• Having non-technical companies as clients was better since they don’t really care about the underlying tech that you’re building for them.
• People who are good software engineers are great writers who can organize their thoughts and communicate.
• Karl Marx spoke about alienation from the customer if you’re a factory worker who sits in a dungeon compared to a craftsman who interacts with the customer to get a fruitful outcome.
• Going public - underwriters get paid the more deals they do, and they’d rather prefer doing deals with big VC-backed firms because they have to do less due diligience.
• You can’t turn an employee into a businessman because the employee only cares about making his boss happy while the businessman cares about the customer.
• McKinsey says that they’ll never grow a company by more than 25 percent per year because otherwise it’s too hard to transmit the corporate culture.
• In ArsDigita’s case, the VCs controlled majority of the board and pushed the founder out, but the founder still owned a majority stake, and since shareholders elect the board, he was able to elect himself back in. VCs could sue, but they would have to pay for it from their own pockets, which VCs hate doing (they would rather spend the money of the limited partners e.g., pension funds). But the VCs got the ex-CEO to illegally write them a cheque and they sued the founder with his own company’s cash- this would be a long court battle for the founder.
• Mythical man-month - they second system ships much later than you expect. Because the first system has all these weaknesses but they exist because they’re hard to solve and these were tradeoffs that were made. The second system is trying to fix these weaknesses but the problems are still fundamentally difficult to solve.
• People will remember how you made them feel more than what you said.
• Consulting market is derivative of every other market. When a company is growing rapidly, they will hire a few consultants to help them grow. When they shrink even a tiny bit, the first people to go are the consultants.
• Why listen to our customers indirectly through our competitors when we can just talk to our customers?
• Even if a deal is lost, it is worth it to persist.
• Existing companies biggest problem is legacy- they can’t focus on new businesses because they’ve got to manage old ones.
• Success is 50% luck and 50% preparedness for that luck.
• It is surprising how well companies can do if you challenge them with these big, crazy goals.
• Hiring slowly and more carefully is important.
• You have to be willing to move move on, even if you’ve got real success.
• Treat your customer how you’d like to be treated.
• You’d be surprised that there are a lot of people rooting for you to be successful.
• Competitors rarely kill companies. Usually they’re self-inflicted wounds.