I wanted to start highlighting some of the things that stood out to be while listening to podcasts each month. Just kind of seeing where this goes - not sure if it will be interesting at all. There's not a ton as I had the idea late in the month but here goes...
Steli talks about having the confidence to say no to something that potential enterprise customers ask for. You know you're handicapping your potential growth to some degree, but in exchange you get to build something you actually enjoy working on. He says "how much money would someone have to pay you to be bored the rest of your life. Or marry someone you don’t want to.”
To be this segment is a good reminder that growth at all costs doesn't have to be the only focus of a business. Particularly if you don't go down the VC route. You can maintain more control and build the company that you actually want to build-- that makes you happy. It reminds me very much of the book Small Giants.
Steli talks about thinking about people as lifelong relationships instead of a series of transactions - particularly in sales. Thinking about customers as not customers just for the business, but as your potential lifelong relationships, customers for things you do in the future, partners. He says to [ick one person a week that you think they’ll do awesome things in their life - like you’d want to invest in this person inc. and treat them as someone you want to nurture a relationship for the rest of their life. You’ll get so much more as these relationships turn into friendships instead of just a transaction that has a short life. Best time to plant a tree is 20 years ago. Second best time is the today. Start putting in the work now because time goes fast and this work will accumulate.
This resonated with me a lot because I've recently been having a lot of regrets around not putting in more work fostering relationships with folks at Atlassian. Those years were an opportunity to branch out and build more friendships and I kind of just phoned it in and only hung out with the Statuspage team.
Mike talks for a while about this thoughts on Inflections. These are the reason why “now” is the right time for a startup idea to work. It’s the wave you ride. There are five different types: technology inflections (Moore’s law, speed of bandwidth, accuracy of gps), adoption inflections (smartphone penetration), regulatory inflections (telemedicine across state lines), belief inflections (work from home becomes mainstream), and paradigm inflections (ideas invented that step change things: Bitcoin). To have insights into the emergence of inflection points you have to "live in the future" at the edge of these infections. For example, he suggests working at a remote company and see what the future of work should be for everyone.
They talk a lot about not evaluating startup ideas based on the size of the current market because it doesn’t exist yet (Uber, etc.). I'm still developing my thoughts on this but as a counter example, lots of huge companies are the Nth into a space (Slack, Notion, Drift) and grow that space (as opposed to "inventing" something new like Uber). It seems like maybe he would say that you can have a similar line of thinking for both non-existent markets and undeveloped markets. It can be hard to see that a market that has existed for several years (Hipchat) might grow 10x or 100x if the experience was better, it was designed just a bit different, etc.. Just something to think about.
The "living in the future" idea from Mike Maples must have still been on my mind. They were talking about how much luck is involved in finding the right "timing" for an idea -- while I agree that luck plays some part I think the majority of the credit goes to developing an intuition for what the future could be. You do this by living in the future (working at a remote startup, working on developing new technologies, etc.) and really giving a damn about what's going on around you. It's easy to fall into the trap of going to work and just fulfilling the requirements of your role. But it's hard work to take a step back and look at all the things around your day-to-day -- how are the processes your team follows working for your company, how do the tools you use enable you to do your best, how is the market your product is in changing and where might it go in the future? Intentionally thinking and caring about these kinds questions is hard work but it leads to the kinds of insights that are required to know that "now is the perfect time to start a business around ______".