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Mar 29, 2019 · 32m · 20vc

20VC: Buffer's Joel Gascoigne on The Moment The Founder Is No Longer The Boss, The Questions Founders Must Ask Their VCs and Why We Need A Spectrum of Different Financing Mechanisms Other Than VC

Joel Gascoigne · 21m spoken Harry Stebbings · 10m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, Buffer co-founder and CEO Joel Gascoigne joins Harry Stebbings to discuss building a sustainable software company, the realities of venture capital control, buying out investors to regain autonomy, and leading with radical transparency.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 32.8% of the talking time here. How this is scored →

Harry as informed peer 5.0 Guest teaching 4.3 Guest disagreement 2.0 Harry pushing back 3.7
05100:0010:0020:0030:003:22–6:12 · Harry as informed peer 3/10 Joel Gascoigne's Early Career and Buffer's Origins Harry opens with warm praise and asks standard origin questions about Joel's early coding background and the founding of Buffer. Joel answers in an easygoing, conversational manner without any friction or debate.6:12–10:23 · Harry as informed peer 5/10 The Realities of VC Fundraising and Loss of Founder Control Joel highlights how fundraising often strips founders of control once board seats flip to investors. Harry probes deeper, asking Joel to pinpoint the exact personal moment he felt he was no longer his own boss, prompting Joel to detail buying out Series A investors.10:23–14:23 · Harry as informed peer 7/10 VC Incentives and Alternative Financing Models Harry demonstrates industry expertise by quoting Anand Sanwal's 'foie gras' startup metaphor and pressing Joel on what founders fail to understand about VC mechanics as an asset class. Joel expands on the structural misalignment between standard VC growth mandates and sustainable business models.14:23–20:02 · Harry as informed peer 6/10 Balancing Profitability, Margins, and Growth Velocity Harry challenges Joel's philosophical idea of aligning a company with what 'lights you up,' pushing back on whether founders actually have the luxury to do so when managing employees' livelihoods. Joel responds by demonstrating how maintaining profitability yields that exact optionality.20:02–24:06 · Harry as informed peer 5/10 Transitioning to Solo Leadership and Finding Support Harry asks a direct personal question regarding an investor suggesting Joel step down as CEO. Joel describes how the misalignment in goals led to the buyout, and Harry offers advice on executive coaching.24:06–29:41 · Harry as informed peer 4/10 The Philosophy and Power of Radical Transparency Joel explains his philosophy of radical transparency to avoid treating employees like children during hard times. Harry guides the conversation through a quick-fire round covering books, remote work, and long-term profit sharing.3:22–6:12 · Guest teaching 2/10 Joel Gascoigne's Early Career and Buffer's Origins Harry opens with warm praise and asks standard origin questions about Joel's early coding background and the founding of Buffer. Joel answers in an easygoing, conversational manner without any friction or debate.6:12–10:23 · Guest teaching 5/10 The Realities of VC Fundraising and Loss of Founder Control Joel highlights how fundraising often strips founders of control once board seats flip to investors. Harry probes deeper, asking Joel to pinpoint the exact personal moment he felt he was no longer his own boss, prompting Joel to detail buying out Series A investors.10:23–14:23 · Guest teaching 6/10 VC Incentives and Alternative Financing Models Harry demonstrates industry expertise by quoting Anand Sanwal's 'foie gras' startup metaphor and pressing Joel on what founders fail to understand about VC mechanics as an asset class. Joel expands on the structural misalignment between standard VC growth mandates and sustainable business models.14:23–20:02 · Guest teaching 5/10 Balancing Profitability, Margins, and Growth Velocity Harry challenges Joel's philosophical idea of aligning a company with what 'lights you up,' pushing back on whether founders actually have the luxury to do so when managing employees' livelihoods. Joel responds by demonstrating how maintaining profitability yields that exact optionality.20:02–24:06 · Guest teaching 4/10 Transitioning to Solo Leadership and Finding Support Harry asks a direct personal question regarding an investor suggesting Joel step down as CEO. Joel describes how the misalignment in goals led to the buyout, and Harry offers advice on executive coaching.24:06–29:41 · Guest teaching 4/10 The Philosophy and Power of Radical Transparency Joel explains his philosophy of radical transparency to avoid treating employees like children during hard times. Harry guides the conversation through a quick-fire round covering books, remote work, and long-term profit sharing.3:22–6:12 · Guest disagreement 1/10 Joel Gascoigne's Early Career and Buffer's Origins Harry opens with warm praise and asks standard origin questions about Joel's early coding background and the founding of Buffer. Joel answers in an easygoing, conversational manner without any friction or debate.6:12–10:23 · Guest disagreement 2/10 The Realities of VC Fundraising and Loss of Founder Control Joel highlights how fundraising often strips founders of control once board seats flip to investors. Harry probes deeper, asking Joel to pinpoint the exact personal moment he felt he was no longer his own boss, prompting Joel to detail buying out Series A investors.10:23–14:23 · Guest disagreement 3/10 VC Incentives and Alternative Financing Models Harry demonstrates industry expertise by quoting Anand Sanwal's 'foie gras' startup metaphor and pressing Joel on what founders fail to understand about VC mechanics as an asset class. Joel expands on the structural misalignment between standard VC growth mandates and sustainable business models.14:23–20:02 · Guest disagreement 2/10 Balancing Profitability, Margins, and Growth Velocity Harry challenges Joel's philosophical idea of aligning a company with what 'lights you up,' pushing back on whether founders actually have the luxury to do so when managing employees' livelihoods. Joel responds by demonstrating how maintaining profitability yields that exact optionality.20:02–24:06 · Guest disagreement 3/10 Transitioning to Solo Leadership and Finding Support Harry asks a direct personal question regarding an investor suggesting Joel step down as CEO. Joel describes how the misalignment in goals led to the buyout, and Harry offers advice on executive coaching.24:06–29:41 · Guest disagreement 1/10 The Philosophy and Power of Radical Transparency Joel explains his philosophy of radical transparency to avoid treating employees like children during hard times. Harry guides the conversation through a quick-fire round covering books, remote work, and long-term profit sharing.3:22–6:12 · Harry pushing back 0/10 Joel Gascoigne's Early Career and Buffer's Origins Harry opens with warm praise and asks standard origin questions about Joel's early coding background and the founding of Buffer. Joel answers in an easygoing, conversational manner without any friction or debate.6:12–10:23 · Harry pushing back 4/10 The Realities of VC Fundraising and Loss of Founder Control Joel highlights how fundraising often strips founders of control once board seats flip to investors. Harry probes deeper, asking Joel to pinpoint the exact personal moment he felt he was no longer his own boss, prompting Joel to detail buying out Series A investors.10:23–14:23 · Harry pushing back 5/10 VC Incentives and Alternative Financing Models Harry demonstrates industry expertise by quoting Anand Sanwal's 'foie gras' startup metaphor and pressing Joel on what founders fail to understand about VC mechanics as an asset class. Joel expands on the structural misalignment between standard VC growth mandates and sustainable business models.14:23–20:02 · Harry pushing back 6/10 Balancing Profitability, Margins, and Growth Velocity Harry challenges Joel's philosophical idea of aligning a company with what 'lights you up,' pushing back on whether founders actually have the luxury to do so when managing employees' livelihoods. Joel responds by demonstrating how maintaining profitability yields that exact optionality.20:02–24:06 · Harry pushing back 5/10 Transitioning to Solo Leadership and Finding Support Harry asks a direct personal question regarding an investor suggesting Joel step down as CEO. Joel describes how the misalignment in goals led to the buyout, and Harry offers advice on executive coaching.24:06–29:41 · Harry pushing back 2/10 The Philosophy and Power of Radical Transparency Joel explains his philosophy of radical transparency to avoid treating employees like children during hard times. Harry guides the conversation through a quick-fire round covering books, remote work, and long-term profit sharing.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 100% · guest 0%0:00 · Harry 100% · guest 0%3:00 · Harry 22.5% · guest 77.5%3:00 · Harry 22.5% · guest 77.5%6:00 · Harry 14.5% · guest 85.5%6:00 · Harry 14.5% · guest 85.5%9:00 · Harry 19.6% · guest 80.4%9:00 · Harry 19.6% · guest 80.4%12:00 · Harry 20% · guest 80%12:00 · Harry 20% · guest 80%15:00 · Harry 18% · guest 82%15:00 · Harry 18% · guest 82%18:00 · Harry 19.7% · guest 80.3%18:00 · Harry 19.7% · guest 80.3%21:00 · Harry 17.1% · guest 82.9%21:00 · Harry 17.1% · guest 82.9%24:00 · Harry 23.1% · guest 76.9%24:00 · Harry 23.1% · guest 76.9%27:00 · Harry 25.5% · guest 74.5%27:00 · Harry 25.5% · guest 74.5%30:00 · Harry 100% · guest 0%30:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 20:08 Rejection of investor pressure to step down

Joel firmly rejects an investor's premise that he should step down as CEO, noting that the investor was not on the board and that their goals were fundamentally misaligned.

 Hardest push from Harry ▶ 17:52 Challenge on founder luxury versus employee responsibility

Harry directly challenges Joel's notion of doing what 'lights you up', asking if founders with dozens of employees actually have the luxury to pivot based on personal excitement.

 Biggest teaching moment ▶ 6:34 Breakdown of lost founder control and cap table dynamics

Joel educates the audience on the subtle mechanics of venture rounds, explaining how board flips and cost of capital quietly strip founders of their autonomy before they even realize it.

 Harry holds his own ▶ 10:23 Industry commentary on VC overfeeding

Harry demonstrates deep knowledge of venture capital dynamic trends by introducing Anand Sanwal's concept of 'foie gras' startups to evaluate manufactured growth rates.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Joel Gascoigne's Early Career and Buffer's Origins 3210 Harry opens with warm praise and asks standard origin questions about Joel's early coding background and the founding of Buffer. Joel answers in an easygoing, conversational manner without any friction or debate.
The Realities of VC Fundraising and Loss of Founder Control 5524 Joel highlights how fundraising often strips founders of control once board seats flip to investors. Harry probes deeper, asking Joel to pinpoint the exact personal moment he felt he was no longer his own boss, prompting Joel to detail buying out Series A investors.
VC Incentives and Alternative Financing Models 7635 Harry demonstrates industry expertise by quoting Anand Sanwal's 'foie gras' startup metaphor and pressing Joel on what founders fail to understand about VC mechanics as an asset class. Joel expands on the structural misalignment between standard VC growth mandates and sustainable business models.
Balancing Profitability, Margins, and Growth Velocity 6526 Harry challenges Joel's philosophical idea of aligning a company with what 'lights you up,' pushing back on whether founders actually have the luxury to do so when managing employees' livelihoods. Joel responds by demonstrating how maintaining profitability yields that exact optionality.
Transitioning to Solo Leadership and Finding Support 5435 Harry asks a direct personal question regarding an investor suggesting Joel step down as CEO. Joel describes how the misalignment in goals led to the buyout, and Harry offers advice on executive coaching.
The Philosophy and Power of Radical Transparency 4412 Joel explains his philosophy of radical transparency to avoid treating employees like children during hard times. Harry guides the conversation through a quick-fire round covering books, remote work, and long-term profit sharing.

Statements from this episode (9)

Assertion Supported
Buffer spent $3.3M to buy out majority of Series A investors
“And they had raised both seed and Series A rounds, but last summer, they spent 3.3 million dollars to buy out the majority of their Series A investors, making them much more independent.”
Harry Stebbings Mar 29, 2019 ▶ 0:30
Assertion Supported
Buffer generated $2M in profit in 2017 and $3M in 2018
“Today, Joel runs Buffer as a profitable business, with two million in profit in 2017, and three million in profit in 2018.”
Harry Stebbings Mar 29, 2019 ▶ 0:39
Insight
Gascoigne: Buffer's founding insight was preset daily social media schedules
“I started to schedule using TweetDeck and Hootsuite at the time, but you had to choose a very specific date and time every time you were scheduling something. And all I really cared about was spacing out the tweets there. So that was the aha moment was, oh, I …”
Joel Gascoigne Mar 29, 2019 ▶ 5:42
Insight
Gascoigne: Startup boards usually flip to investor control by Series B
“And I think at some point along the way, maybe it's series A, series B, the board usually flips over to be controlled by investors.”
Joel Gascoigne Mar 29, 2019 ▶ 7:08
Disclosure
Buffer gave no board seats to investors in seed or Series A
“So both rounds, we didn't bring any investors on the board.”
Joel Gascoigne Mar 29, 2019 ▶ 10:18
Assertion Not checkable as stated
Gascoigne: VC incentives drive overfunding startups to see what happens
“The way the VCs are set up generally is structured towards basically triggering an environment where it is almost better if they can pump up these startups, put a lot of money into them, and just kind of see what happens, see if it works, and 90% of the time i…”
Joel Gascoigne Mar 29, 2019 ▶ 11:00
Insight
Gascoigne: VC forces startups into a rollercoaster of 100% annual growth
“For the longest time, the only option has been VC. And then the only option is that you lock yourself into this white knuckle ride rollercoaster and that the outcome has to be this a hundred percent year over year growth for the longest time. And I think there…”
Joel Gascoigne Mar 29, 2019 ▶ 13:08
Insight
Gascoigne: Withholding financial details from employees treats them like children
“I think sometimes as leaders, we almost treat our team as children or something, you know, that they can't handle those details or that truth Or something. And I think that's just really a disservice to everyone that you've brought on board. Like everyone is a…”
Joel Gascoigne Mar 29, 2019 ▶ 25:22
Disclosure
Buffer uses profit sharing to help buy out short-term investors
“We've been doing profit sharing for two years in a row now, and we want to keep going more in those directions and helping investors get liquidity when they're more interested in kind of a short-term horizon so that we can become more self-owned over time and …”
Joel Gascoigne Mar 29, 2019 ▶ 29:07
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