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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.
Matt Mochary has been CEO coach to @naval, the founders of OpenAI, Notion, Rippling, Robinhood, Coinbase, Reddit, Plaid, Flexport, Opendoor, partners at Sequoia, YC, Benchmark, and many others.
He also open-sourced his entire curriculum, templates and all. Here's a link 👇
The Mochary Method Curriculum ➔ https://t.co/A8J51IzYhz
My recent conversation with @mattmochary where we talk about fear, anger, innovation, how to lay people off well, and his coaching practice ➔
Also in podcast form ➔
For more from Matt, buy this book
He also open-sourced his entire curriculum, templates and all. Here's a link 👇

The Mochary Method Curriculum ➔ https://t.co/A8J51IzYhz
My recent conversation with @mattmochary where we talk about fear, anger, innovation, how to lay people off well, and his coaching practice ➔
Also in podcast form ➔
For more from Matt, buy this book
1/ I feel like breaking some rules today. Let's get transparent and have an open discussion about management fees in VC to help other emerging managers. The standard fee structure is 2% the size of the fund every year for 10 years or the life of the fund.
#vc #startups #funding
2/ This means if you are an emerging manager raising a micro/nano fund of let's say $10M, then you get $200K a year for operations. That $200K pays for legal, fund admin, accounting, expenses, and your salary. basically that 2% doesn't go very far
#vc #startups #funding
3/ This is in contrast to a larger fund, let's say $100M fund where 2% is $2M a year. This is why some LPs (those who invest in funds) are looking for smaller management fee which is unreasonable for micro funds which many diverse managers are raising
#vc #startups #funding
4/ Now at RareBreed Ventures we structured our fees to be 2.5% for the first 5 years and 1.5% for the last 5 years. This comes out to the standard 2% but front-loaded in earlier years
#vc #startups #funding
5/ This means when we hit our target of $10M (if you want to be an LP our min investment is 10K and you can go to https://t.co/dm6ywrNFnU). We'll have 250K for the first 5 years giving a little more cushion for operations and allowing me to bring on a hire
#vc #startups #funding
#vc #startups #funding
2/ This means if you are an emerging manager raising a micro/nano fund of let's say $10M, then you get $200K a year for operations. That $200K pays for legal, fund admin, accounting, expenses, and your salary. basically that 2% doesn't go very far
#vc #startups #funding
3/ This is in contrast to a larger fund, let's say $100M fund where 2% is $2M a year. This is why some LPs (those who invest in funds) are looking for smaller management fee which is unreasonable for micro funds which many diverse managers are raising
#vc #startups #funding
4/ Now at RareBreed Ventures we structured our fees to be 2.5% for the first 5 years and 1.5% for the last 5 years. This comes out to the standard 2% but front-loaded in earlier years
#vc #startups #funding
5/ This means when we hit our target of $10M (if you want to be an LP our min investment is 10K and you can go to https://t.co/dm6ywrNFnU). We'll have 250K for the first 5 years giving a little more cushion for operations and allowing me to bring on a hire
#vc #startups #funding