Regarding the scripted pitch: try dumping your brain about your product into ChatGPT and ask it to “generate an elevator pitch for the following product description”. Sometimes it does a great job. Other times it at least gives you insight.

I’m an experienced software developer who’s just dipping his toes into entrepreneurship again. I don’t mind moving fast - I’ve had to do that plenty! But I’m also a sucker for quality, security, performance so I need to remind myself what I’m doing sometimes. I’m currently building something simple that is somewhat niche but proven market then use it to learn more about the sales & marketing side of things. It’s a product that’s centered around security so I have been taking my time with it especially since it’s relatively small. Then I’ll be more well equipped for a larger undertaking. At least that’s my plan!

Interesting take! I don’t think you’re wrong - just a surprise.

Absolutely. You want to evaluate their ability to pull this off. Are they really good at sales and marketing? Do they make good financial decisions? What qualifications do they have for being the CEO? Why are they not getting a loan to pay your salary and keeping 100% ownership? Who else are they hiring? How have they diluted the company in other areas? How good are these potential customers and the idea? What roles will be expected of you long-term? Will these stocks pay dividends? When? What other compensation is laid out for the future when the company becomes profitable? What happens if the cofounder leaves? (That’ll be covered by a good agreement along with other contingencies)

You certainly don’t want to be holding their hand through the process. Especially if you have less than 50% equity.

My boss at my day job is not a developer. He absolutely crushes sales and managing a team of developers who are passionate about working for him. It’s 100% possible to be a CEO, a salesperson, or whatever role without being a programmer. They just need to consult and trust their developers.

First of all, congratulations on all the success you’ve created! It sounds like the failures in the startups were not due to your influence (quite the contrary). So I’d give yourself a lot more credit.

If you don’t feel the need for speed any more (understandable), I’m sure you could secure a potentially more stable position… but a lot of places are experiencing hardship right now so I’m not sure how stable any of them are.

You’ve done a lot of hiring so: would you hire you? If not, why not? I’d at least interview you. You have a lot of experience working with different types of teams and that can be invaluable.

Take a week off from the anxiety. Get a massage. Center yourself. Your mind is just burnt out from your last position. Stop the negative self-talk. You’re killing it. Cheers

Why not do analysis or talk to CEOs at some of these large companies and see what they actually need? Airtable is no small feat even for a well oiled machine… and (making an assumption here) you have no specific use cases to build it around so you’re shooting in the dark.

Are you a solo dev or are you building a team? Honestly, if I were to build something as big as Airtable today, I’d be doing so with ChatGPT integration so I could write a user story and produce a workflow. To pull that off, you need a good visionary on your team who isn’t afraid to break all the rules and pull off something astounding.

I’m a seasoned developer with a boss (CEO) who’s not one. Definitely stay out of software. It’s an advantage when problem solving because you’re not constrained by the tech and it’s great when you’re on a conference call to say you’ll talk it over with the developers and get back to them. Focus on sales, marketing, making a great work environment. One of the reasons I’ve been there 20 years is: it’s a flat organizational structure and nobody is blamed when there’s a problem. We just work to solve it. We crush big challenges and are appreciated for our hard work. Always have great dev PCs, all the books we want, and the best tools. Keep things light, isolate as much of the outer hostilities from your team as possible, trust your team, and people will enjoy working their ***es off for you.