1/ The first 18 months of starting a company is often life or death. I must've made 5 different companies that each failed within 9 mo. 😭 Each time the company failed I figured out what I could do better. Eventually startup #6 got to $40K/mo by month 18. Here’s what I learned...

1/ I became "CEO" at 20. I dropped out of college. I had only interned somewhere prev. Looking back, I couldn't imagine the journey that would occur from writing code all day to scaling to 300 people. I got lucky, I screwed up a lot, & had a lot of help. Here's what I learned...
— Suhail (@Suhail) May 21, 2018
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1/ Tuesday was my last day as CEO of @CircleUp. I’ve been CEO since starting the co. in 2011 with my co-founder @roryeakin.
This is a thread about what happened, why and my emotions about it. For more detail:
https://t.co/vYImcm1bTM
Much of this I have never talked about.
2/ My goals: I hope it helps founders feel less lonely than I did. Little public content about the challenges of transitioning exists, but I longed for it. I’m not here to provide a playbook- just to share my experience. Hope it might build greater empathy.
Here goes….
3/ Why: When I tell people that I’m transitioning to an Exec Chairman role their first question is always: “why?” Short answer: co. pivot + fertility issues + health issues + a false sense that grit was always the answer = burnout. Long answer: is longer so hang in there with me
4/ Over a 12-18 month period that ended in late 2017 I ran my tank far beyond empty for far too long. You know that sound your car makes when it’s sputtering for more gas? It was like that. Worst year of my life. Since then it has felt like bone on bone.
5/ Here is what happened:
Professionally: pivoting a Series C company was a living hell in and of itself, as I’ve talked about before.
This is a thread about what happened, why and my emotions about it. For more detail:
https://t.co/vYImcm1bTM
Much of this I have never talked about.
2/ My goals: I hope it helps founders feel less lonely than I did. Little public content about the challenges of transitioning exists, but I longed for it. I’m not here to provide a playbook- just to share my experience. Hope it might build greater empathy.
Here goes….
3/ Why: When I tell people that I’m transitioning to an Exec Chairman role their first question is always: “why?” Short answer: co. pivot + fertility issues + health issues + a false sense that grit was always the answer = burnout. Long answer: is longer so hang in there with me
4/ Over a 12-18 month period that ended in late 2017 I ran my tank far beyond empty for far too long. You know that sound your car makes when it’s sputtering for more gas? It was like that. Worst year of my life. Since then it has felt like bone on bone.
5/ Here is what happened:
Professionally: pivoting a Series C company was a living hell in and of itself, as I’ve talked about before.
1/ We Pivoted a few yrs ago. This is the story- mostly my feelings. It has never been told publicly.
— Ryan Caldbeck (@ryan_caldbeck) April 16, 2019
This will be rambly and represents the chaos in my head at the time. There is [hopefully] no advice here. I don\u2019t know if we did it right.
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To people who are under the impression that you can get rich quickly by working on an app, here are the stats for https://t.co/az8F12pf02
📈 ~12000 vistis
☑️ 109 transactions
💰 353€ profit (285 after tax)
I have spent 1.5 months on this app. You can make more $ in 2 days.
🤷♂️
I'm still happy that I launched a paid app bcs it involved extra work:
- backend for processing payments (+ permissions, webhooks, etc)
- integration with payment processor
- UI for license activation in Electron
- machine activation limit
- autoupdates
- mailgun emails
etc.
These things seemed super scary at first. I always thought it was way too much work and something would break. But I'm glad I persisted. So far the only problem I have is that mailgun is not delivering the license keys to certain domains like https://t.co/6Bqn0FUYXo etc. 👌
omg I just realized that me . com is an Apple domain, of course something wouldn't work with these dicks
📈 ~12000 vistis
☑️ 109 transactions
💰 353€ profit (285 after tax)
I have spent 1.5 months on this app. You can make more $ in 2 days.
🤷♂️

I'm still happy that I launched a paid app bcs it involved extra work:
- backend for processing payments (+ permissions, webhooks, etc)
- integration with payment processor
- UI for license activation in Electron
- machine activation limit
- autoupdates
- mailgun emails
etc.
These things seemed super scary at first. I always thought it was way too much work and something would break. But I'm glad I persisted. So far the only problem I have is that mailgun is not delivering the license keys to certain domains like https://t.co/6Bqn0FUYXo etc. 👌
omg I just realized that me . com is an Apple domain, of course something wouldn't work with these dicks