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Dec 23, 2016 · 29m · 20vc

20VC: What VCs Really Mean They Say 'Stay In Touch', Why Incentivisation Through Perks Is Lazy & Why Founders Should Always Under-Promise & Over-Deliver with David Politis, Founder @ CEO @ Bettercloud

David Politis · 21m spoken Harry Stebbings · 7m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews David Politis, founder and CEO of BetterCloud, about his entrepreneurial journey, executive leadership lessons, and scaling enterprise SaaS startups. David shares insights on venture capital fundraising, building authentic company culture without relying on superficial perks, and executing a bold long-term product vision.

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 25.2% of the talking time here. How this is scored →

Harry as informed peer 2.0 Guest teaching 4.1 Guest disagreement 0.1 Harry pushing back 0.8
05100:0010:0020:002:29–5:03 · Harry as informed peer 1/10 Welcome and David Politis' Early Career Journey Harry opens with standard background questions. David shares his origin story, detailing how he became CEO of Vocalocity at a young age following mass layoffs and pivoted the company.5:08–7:32 · Harry as informed peer 2/10 Key Lessons Learned as a Young First-Time CEO Harry interject to redirect David from his timeline to focus on key lessons learned as a first-time CEO. David shares insights on trusting intuition and learning from early organizational mistakes.7:37–11:04 · Harry as informed peer 1/10 The Founding Story and Market Need for BetterCloud David explains the founding narrative of BetterCloud, describing how his time at CloudSherpas highlighted the missing IT management infrastructure for SaaS applications.11:08–13:38 · Harry as informed peer 4/10 Workplace Culture versus Superfluous Employee Perks Harry demonstrates preparation by bringing up David's past statement regarding non-perk investments. David forcefully critiques perk-heavy workplace cultures as superficial and lazy.13:39–19:48 · Harry as informed peer 2/10 Building a Deliberate Culture and Management Accountability David delivers an extended explanation on building scaling culture, introducing initiatives like transparent 360 leadership sessions and monthly peer recognition awards.19:49–22:11 · Harry as informed peer 3/10 The Evolution of Fundraising Across Company Growth Stages Harry cites specific fundraising numbers, prompting David to reflect on fundraising evolutions across stages and explaining how VCs politely brush off founders with 'stay in touch'.22:12–24:18 · Harry as informed peer 2/10 Investor Syndicate Strategy and Under-Promising Vision David reflects candidly on investor syndicate composition and admits his tendency to under-promise led him to under-pitch BetterCloud's long-term vision during early fundraising rounds.24:21–26:40 · Harry as informed peer 2/10 Quick-Fire Insights: Reading, Leadership, and Mindset Harry guides David through rapid-fire questions covering reading material, lessons learned, and management evolution in a collaborative format.26:45–27:28 · Harry as informed peer 1/10 BetterCloud's Five-Year Vision and Interview Conclusion David outlines BetterCloud's 5-year outlook to become the core control center for corporate SaaS applications before Harry wraps up the episode.2:29–5:03 · Guest teaching 3/10 Welcome and David Politis' Early Career Journey Harry opens with standard background questions. David shares his origin story, detailing how he became CEO of Vocalocity at a young age following mass layoffs and pivoted the company.5:08–7:32 · Guest teaching 4/10 Key Lessons Learned as a Young First-Time CEO Harry interject to redirect David from his timeline to focus on key lessons learned as a first-time CEO. David shares insights on trusting intuition and learning from early organizational mistakes.7:37–11:04 · Guest teaching 5/10 The Founding Story and Market Need for BetterCloud David explains the founding narrative of BetterCloud, describing how his time at CloudSherpas highlighted the missing IT management infrastructure for SaaS applications.11:08–13:38 · Guest teaching 5/10 Workplace Culture versus Superfluous Employee Perks Harry demonstrates preparation by bringing up David's past statement regarding non-perk investments. David forcefully critiques perk-heavy workplace cultures as superficial and lazy.13:39–19:48 · Guest teaching 6/10 Building a Deliberate Culture and Management Accountability David delivers an extended explanation on building scaling culture, introducing initiatives like transparent 360 leadership sessions and monthly peer recognition awards.19:49–22:11 · Guest teaching 5/10 The Evolution of Fundraising Across Company Growth Stages Harry cites specific fundraising numbers, prompting David to reflect on fundraising evolutions across stages and explaining how VCs politely brush off founders with 'stay in touch'.22:12–24:18 · Guest teaching 4/10 Investor Syndicate Strategy and Under-Promising Vision David reflects candidly on investor syndicate composition and admits his tendency to under-promise led him to under-pitch BetterCloud's long-term vision during early fundraising rounds.24:21–26:40 · Guest teaching 3/10 Quick-Fire Insights: Reading, Leadership, and Mindset Harry guides David through rapid-fire questions covering reading material, lessons learned, and management evolution in a collaborative format.26:45–27:28 · Guest teaching 2/10 BetterCloud's Five-Year Vision and Interview Conclusion David outlines BetterCloud's 5-year outlook to become the core control center for corporate SaaS applications before Harry wraps up the episode.2:29–5:03 · Guest disagreement 0/10 Welcome and David Politis' Early Career Journey Harry opens with standard background questions. David shares his origin story, detailing how he became CEO of Vocalocity at a young age following mass layoffs and pivoted the company.5:08–7:32 · Guest disagreement 0/10 Key Lessons Learned as a Young First-Time CEO Harry interject to redirect David from his timeline to focus on key lessons learned as a first-time CEO. David shares insights on trusting intuition and learning from early organizational mistakes.7:37–11:04 · Guest disagreement 0/10 The Founding Story and Market Need for BetterCloud David explains the founding narrative of BetterCloud, describing how his time at CloudSherpas highlighted the missing IT management infrastructure for SaaS applications.11:08–13:38 · Guest disagreement 1/10 Workplace Culture versus Superfluous Employee Perks Harry demonstrates preparation by bringing up David's past statement regarding non-perk investments. David forcefully critiques perk-heavy workplace cultures as superficial and lazy.13:39–19:48 · Guest disagreement 0/10 Building a Deliberate Culture and Management Accountability David delivers an extended explanation on building scaling culture, introducing initiatives like transparent 360 leadership sessions and monthly peer recognition awards.19:49–22:11 · Guest disagreement 0/10 The Evolution of Fundraising Across Company Growth Stages Harry cites specific fundraising numbers, prompting David to reflect on fundraising evolutions across stages and explaining how VCs politely brush off founders with 'stay in touch'.22:12–24:18 · Guest disagreement 0/10 Investor Syndicate Strategy and Under-Promising Vision David reflects candidly on investor syndicate composition and admits his tendency to under-promise led him to under-pitch BetterCloud's long-term vision during early fundraising rounds.24:21–26:40 · Guest disagreement 0/10 Quick-Fire Insights: Reading, Leadership, and Mindset Harry guides David through rapid-fire questions covering reading material, lessons learned, and management evolution in a collaborative format.26:45–27:28 · Guest disagreement 0/10 BetterCloud's Five-Year Vision and Interview Conclusion David outlines BetterCloud's 5-year outlook to become the core control center for corporate SaaS applications before Harry wraps up the episode.2:29–5:03 · Harry pushing back 0/10 Welcome and David Politis' Early Career Journey Harry opens with standard background questions. David shares his origin story, detailing how he became CEO of Vocalocity at a young age following mass layoffs and pivoted the company.5:08–7:32 · Harry pushing back 2/10 Key Lessons Learned as a Young First-Time CEO Harry interject to redirect David from his timeline to focus on key lessons learned as a first-time CEO. David shares insights on trusting intuition and learning from early organizational mistakes.7:37–11:04 · Harry pushing back 0/10 The Founding Story and Market Need for BetterCloud David explains the founding narrative of BetterCloud, describing how his time at CloudSherpas highlighted the missing IT management infrastructure for SaaS applications.11:08–13:38 · Harry pushing back 3/10 Workplace Culture versus Superfluous Employee Perks Harry demonstrates preparation by bringing up David's past statement regarding non-perk investments. David forcefully critiques perk-heavy workplace cultures as superficial and lazy.13:39–19:48 · Harry pushing back 1/10 Building a Deliberate Culture and Management Accountability David delivers an extended explanation on building scaling culture, introducing initiatives like transparent 360 leadership sessions and monthly peer recognition awards.19:49–22:11 · Harry pushing back 1/10 The Evolution of Fundraising Across Company Growth Stages Harry cites specific fundraising numbers, prompting David to reflect on fundraising evolutions across stages and explaining how VCs politely brush off founders with 'stay in touch'.22:12–24:18 · Harry pushing back 0/10 Investor Syndicate Strategy and Under-Promising Vision David reflects candidly on investor syndicate composition and admits his tendency to under-promise led him to under-pitch BetterCloud's long-term vision during early fundraising rounds.24:21–26:40 · Harry pushing back 0/10 Quick-Fire Insights: Reading, Leadership, and Mindset Harry guides David through rapid-fire questions covering reading material, lessons learned, and management evolution in a collaborative format.26:45–27:28 · Harry pushing back 0/10 BetterCloud's Five-Year Vision and Interview Conclusion David outlines BetterCloud's 5-year outlook to become the core control center for corporate SaaS applications before Harry wraps up the episode.

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

0:00 · Harry 97% · guest 3%0:00 · Harry 97% · guest 3%3:00 · Harry 15.4% · guest 84.6%3:00 · Harry 15.4% · guest 84.6%6:00 · Harry 1.9% · guest 98.1%6:00 · Harry 1.9% · guest 98.1%9:00 · Harry 12.5% · guest 87.5%9:00 · Harry 12.5% · guest 87.5%12:00 · Harry 8.1% · guest 91.9%12:00 · Harry 8.1% · guest 91.9%15:00 · Harry 7.4% · guest 92.6%15:00 · Harry 7.4% · guest 92.6%18:00 · Harry 13% · guest 87%18:00 · Harry 13% · guest 87%21:00 · Harry 6.7% · guest 93.3%21:00 · Harry 6.7% · guest 93.3%24:00 · Harry 14.9% · guest 85.1%24:00 · Harry 14.9% · guest 85.1%27:00 · Harry 86.1% · guest 13.9%27:00 · Harry 86.1% · guest 13.9%
Sharpest disagreement ▶ 11:27 Strong Rejection of Perk Culture

David strongly rejects standard Silicon Valley perk culture, labeling reliance on free meals and perks as lazy, superficial, and fundamentally unhealthy for organizational culture.

 Hardest push from Harry ▶ 5:03 Interruption to Redirect Discussion

Harry interrupts David mid-sentence to stop him from rushing ahead to BetterCloud, insisting that David first detail his core mistakes and learnings as a young CEO.

 Biggest teaching moment ▶ 20:12 Deconstructing VC Rejection Terminology

David educates the host on the hidden subtext of venture capital interactions, pointing out that VCs telling early-stage founders to 'stay in touch' is actually a polite pass.

 Harry holds his own ▶ 11:08 Informed Questioning on Perk Strategy

Harry shows strong guest preparation by quoting David's stance against perks directly back to him, pressing him to defend why perk incentivization is flawed.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Welcome and David Politis' Early Career Journey 1300 Harry opens with standard background questions. David shares his origin story, detailing how he became CEO of Vocalocity at a young age following mass layoffs and pivoted the company.
Key Lessons Learned as a Young First-Time CEO 2402 Harry interject to redirect David from his timeline to focus on key lessons learned as a first-time CEO. David shares insights on trusting intuition and learning from early organizational mistakes.
The Founding Story and Market Need for BetterCloud 1500 David explains the founding narrative of BetterCloud, describing how his time at CloudSherpas highlighted the missing IT management infrastructure for SaaS applications.
Workplace Culture versus Superfluous Employee Perks 4513 Harry demonstrates preparation by bringing up David's past statement regarding non-perk investments. David forcefully critiques perk-heavy workplace cultures as superficial and lazy.
Building a Deliberate Culture and Management Accountability 2601 David delivers an extended explanation on building scaling culture, introducing initiatives like transparent 360 leadership sessions and monthly peer recognition awards.
The Evolution of Fundraising Across Company Growth Stages 3501 Harry cites specific fundraising numbers, prompting David to reflect on fundraising evolutions across stages and explaining how VCs politely brush off founders with 'stay in touch'.
Investor Syndicate Strategy and Under-Promising Vision 2400 David reflects candidly on investor syndicate composition and admits his tendency to under-promise led him to under-pitch BetterCloud's long-term vision during early fundraising rounds.
Quick-Fire Insights: Reading, Leadership, and Mindset 2300 Harry guides David through rapid-fire questions covering reading material, lessons learned, and management evolution in a collaborative format.
BetterCloud's Five-Year Vision and Interview Conclusion 1200 David outlines BetterCloud's 5-year outlook to become the core control center for corporate SaaS applications before Harry wraps up the episode.

Statements from this episode (7)

Assertion Partly supported
Politis became Vocalocity CEO after the firm laid off almost everyone
“Six months after starting that job, they ended up letting go of everyone in the company except for me and one engineer, and so the two of us were left there to build this business. They actually made me CEO of the company.”
David Politis Dec 23, 2016 ▶ 3:37
Insight
Politis: Recruiting and retaining employees via perks is lazy and unhealthy
“In general, I feel like incentivizing or recruiting or retaining people through perks is, is pretty lazy. I think it's superficial. It's unhealthy.”
David Politis Dec 23, 2016 ▶ 11:30
Insight
Startup culture breaks down at 80 employees without deliberate management
“When you get to 80, 90, a hundred people, that's at least where I've seen it, if you're not deliberate about it breaks down. It breaks down because there's just, especially if you think about how many people you've been hiring and how fast, usually at that poi…”
David Politis Dec 23, 2016 ▶ 14:09
Disclosure
BetterCloud requires leaders to share 360 feedback and weaknesses with team
“The key part of this is that the leader has to then take that feedback, good, bad, and ugly, and show it to their entire team. And with that feedback, they also have to tell them what they're going to do to work on their weaknesses.”
David Politis Dec 23, 2016 ▶ 17:42
Disclosure
BetterCloud caused culture shock by introducing ten HR programs simultaneously
“We made a mistake in is we got so excited about being deliberate. We made 80 changes that, you know, I don't know, we made something like we put in 10 people programs at once over a period of a couple months, and it was shock. It just shocked everyone. It was …”
David Politis Dec 23, 2016 ▶ 19:00
Insight
Politis: VCs do not mean it when saying 'stay in touch'
“When people said, oh, this is interesting, you know, stay in touch. I thought they actually meant this is interesting. Stay in touch. They don't, you know, they don't at all.”
David Politis Dec 23, 2016 ▶ 20:26
Assertion Not checkable as stated
Politis failed to articulate BetterCloud's 10-year vision in early fundraising
“I did not do a good job in any round. Really articulating the really, really big vision for BetterCloud. I kind of take this under-promise, over-deliver approach, and I'm just conservative in, in my approach in general, in planning and in, in everything. And s…”
David Politis Dec 23, 2016 ▶ 23:23
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