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Jan 19, 2018 · 22m · 20vc

20VC: Why You Should Not Always Listen To Your Investors, The Pros and Cons of Strategic Investors & How To Approach Operational Efficiency with Scaling with Florian Leibert, Founder & CEO @ Mesosphere

Florian Leibert · 12m spoken Harry Stebbings · 8m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Florian Leibert, Founder and CEO of Mesosphere, joins Harry Stebbings on The 20 Minute VC to discuss his transition from Twitter and Airbnb to building an enterprise infrastructure platform, evaluating strategic corporate investors, and mastering enterprise sales and operational scaling.

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 41.3% of the talking time here. How this is scored →

Harry as informed peer 2.0 Guest teaching 2.2 Guest disagreement 1.0 Harry pushing back 1.0
05100:0010:0020:002:53–7:14 · Harry as informed peer 2/10 Florian Leibert's Background and the Founding of Mesosphere Harry asks standard background questions and prompts Florian about his previous advice on ignoring investors. Florian politely reframes how seed investors pushed for a SaaS model that was completely incompatible with Mesosphere's enterprise data center focus.7:14–11:46 · Harry as informed peer 3/10 Evaluating Strategic Investors: Benefits, Pitfalls, and Timing Harry brings up well-researched quotes from M&A executives like Chad Richard and Alison Goldberg. Florian shares insights on strategic investor channel distribution and reframes the slow-motion M&A premise.11:47–14:23 · Harry as informed peer 3/10 Leveraging Founder Networks and Categorizing Customer Feedback Harry cites Des Treynor regarding the danger of building specific customer requests into product roadmaps. Florian provides a structured framework on clustering data points across 100 enterprise customers to guide roadmap decisions.14:23–17:22 · Harry as informed peer 2/10 Sales Execution, Scaling Sales Teams, and Managing Proof-of-Concepts Harry introduces Jotty Bansal's operational points, asking about sales execution and pilot projects. Florian outlines early hiring mistakes with account executives and stresses defining success metrics prior to pilots.17:28–20:44 · Harry as informed peer 2/10 Building Operational Efficiency and Process at Scale Harry conducts a quickfire round covering process, books, cloud computing, and lessons from Twitter/Airbnb. Florian shares rapid perspectives on edge computing and the essential role of sales in enterprise startups.20:44–22:50 · Harry as informed peer 0/10 Episode Conclusion and Final Advertisements Harry provides a solo monologue closing the episode and reading sponsor announcements. All host-side and guest dynamic scores are 0 for this non-interactive segment.2:53–7:14 · Guest teaching 3/10 Florian Leibert's Background and the Founding of Mesosphere Harry asks standard background questions and prompts Florian about his previous advice on ignoring investors. Florian politely reframes how seed investors pushed for a SaaS model that was completely incompatible with Mesosphere's enterprise data center focus.7:14–11:46 · Guest teaching 2/10 Evaluating Strategic Investors: Benefits, Pitfalls, and Timing Harry brings up well-researched quotes from M&A executives like Chad Richard and Alison Goldberg. Florian shares insights on strategic investor channel distribution and reframes the slow-motion M&A premise.11:47–14:23 · Guest teaching 3/10 Leveraging Founder Networks and Categorizing Customer Feedback Harry cites Des Treynor regarding the danger of building specific customer requests into product roadmaps. Florian provides a structured framework on clustering data points across 100 enterprise customers to guide roadmap decisions.14:23–17:22 · Guest teaching 3/10 Sales Execution, Scaling Sales Teams, and Managing Proof-of-Concepts Harry introduces Jotty Bansal's operational points, asking about sales execution and pilot projects. Florian outlines early hiring mistakes with account executives and stresses defining success metrics prior to pilots.17:28–20:44 · Guest teaching 2/10 Building Operational Efficiency and Process at Scale Harry conducts a quickfire round covering process, books, cloud computing, and lessons from Twitter/Airbnb. Florian shares rapid perspectives on edge computing and the essential role of sales in enterprise startups.20:44–22:50 · Guest teaching 0/10 Episode Conclusion and Final Advertisements Harry provides a solo monologue closing the episode and reading sponsor announcements. All host-side and guest dynamic scores are 0 for this non-interactive segment.2:53–7:14 · Guest disagreement 2/10 Florian Leibert's Background and the Founding of Mesosphere Harry asks standard background questions and prompts Florian about his previous advice on ignoring investors. Florian politely reframes how seed investors pushed for a SaaS model that was completely incompatible with Mesosphere's enterprise data center focus.7:14–11:46 · Guest disagreement 1/10 Evaluating Strategic Investors: Benefits, Pitfalls, and Timing Harry brings up well-researched quotes from M&A executives like Chad Richard and Alison Goldberg. Florian shares insights on strategic investor channel distribution and reframes the slow-motion M&A premise.11:47–14:23 · Guest disagreement 1/10 Leveraging Founder Networks and Categorizing Customer Feedback Harry cites Des Treynor regarding the danger of building specific customer requests into product roadmaps. Florian provides a structured framework on clustering data points across 100 enterprise customers to guide roadmap decisions.14:23–17:22 · Guest disagreement 1/10 Sales Execution, Scaling Sales Teams, and Managing Proof-of-Concepts Harry introduces Jotty Bansal's operational points, asking about sales execution and pilot projects. Florian outlines early hiring mistakes with account executives and stresses defining success metrics prior to pilots.17:28–20:44 · Guest disagreement 1/10 Building Operational Efficiency and Process at Scale Harry conducts a quickfire round covering process, books, cloud computing, and lessons from Twitter/Airbnb. Florian shares rapid perspectives on edge computing and the essential role of sales in enterprise startups.20:44–22:50 · Guest disagreement 0/10 Episode Conclusion and Final Advertisements Harry provides a solo monologue closing the episode and reading sponsor announcements. All host-side and guest dynamic scores are 0 for this non-interactive segment.2:53–7:14 · Harry pushing back 1/10 Florian Leibert's Background and the Founding of Mesosphere Harry asks standard background questions and prompts Florian about his previous advice on ignoring investors. Florian politely reframes how seed investors pushed for a SaaS model that was completely incompatible with Mesosphere's enterprise data center focus.7:14–11:46 · Harry pushing back 2/10 Evaluating Strategic Investors: Benefits, Pitfalls, and Timing Harry brings up well-researched quotes from M&A executives like Chad Richard and Alison Goldberg. Florian shares insights on strategic investor channel distribution and reframes the slow-motion M&A premise.11:47–14:23 · Harry pushing back 2/10 Leveraging Founder Networks and Categorizing Customer Feedback Harry cites Des Treynor regarding the danger of building specific customer requests into product roadmaps. Florian provides a structured framework on clustering data points across 100 enterprise customers to guide roadmap decisions.14:23–17:22 · Harry pushing back 1/10 Sales Execution, Scaling Sales Teams, and Managing Proof-of-Concepts Harry introduces Jotty Bansal's operational points, asking about sales execution and pilot projects. Florian outlines early hiring mistakes with account executives and stresses defining success metrics prior to pilots.17:28–20:44 · Harry pushing back 0/10 Building Operational Efficiency and Process at Scale Harry conducts a quickfire round covering process, books, cloud computing, and lessons from Twitter/Airbnb. Florian shares rapid perspectives on edge computing and the essential role of sales in enterprise startups.20:44–22:50 · Harry pushing back 0/10 Episode Conclusion and Final Advertisements Harry provides a solo monologue closing the episode and reading sponsor announcements. All host-side and guest dynamic scores are 0 for this non-interactive segment.

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

0:00 · Harry 98.4% · guest 1.6%0:00 · Harry 98.4% · guest 1.6%3:00 · Harry 21% · guest 79%3:00 · Harry 21% · guest 79%6:00 · Harry 34.4% · guest 65.6%6:00 · Harry 34.4% · guest 65.6%9:00 · Harry 32.5% · guest 67.5%9:00 · Harry 32.5% · guest 67.5%12:00 · Harry 25.9% · guest 74.1%12:00 · Harry 25.9% · guest 74.1%15:00 · Harry 22.7% · guest 77.3%15:00 · Harry 22.7% · guest 77.3%18:00 · Harry 27.1% · guest 72.9%18:00 · Harry 27.1% · guest 72.9%21:00 · Harry 100% · guest 0%21:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 11:22 Rejecting 'slow motion M&A' premise

Florian explicitly reframes Chad Richard's quote that strategic investment is slow-motion M&A, clarifying that Mesosphere selected strategics purely for sales distribution rather than acquisition potential.

 Hardest push from Harry ▶ 8:06 Challenging strategic investor reseller model

Harry pushes back on the benefits of strategic investor reselling by asking if aligning with one incumbent creates lock-out or exclusivity risks with competing enterprise players.

 Biggest teaching moment ▶ 13:22 Clustering 100 customer data points

Florian educates Harry on product feedback management, explaining that founders must group commonalities across 100 customer interactions rather than building bespoke features for individual clients.

 Harry holds his own ▶ 13:04 Citing Des Treynor on customer feedback traps

Harry demonstrates sector knowledge by citing Intercom founder Des Treynor to challenge Florian on how to gather customer feedback without getting trapped into building custom solutions.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Florian Leibert's Background and the Founding of Mesosphere 2321 Harry asks standard background questions and prompts Florian about his previous advice on ignoring investors. Florian politely reframes how seed investors pushed for a SaaS model that was completely incompatible with Mesosphere's enterprise data center focus.
Evaluating Strategic Investors: Benefits, Pitfalls, and Timing 3212 Harry brings up well-researched quotes from M&A executives like Chad Richard and Alison Goldberg. Florian shares insights on strategic investor channel distribution and reframes the slow-motion M&A premise.
Leveraging Founder Networks and Categorizing Customer Feedback 3312 Harry cites Des Treynor regarding the danger of building specific customer requests into product roadmaps. Florian provides a structured framework on clustering data points across 100 enterprise customers to guide roadmap decisions.
Sales Execution, Scaling Sales Teams, and Managing Proof-of-Concepts 2311 Harry introduces Jotty Bansal's operational points, asking about sales execution and pilot projects. Florian outlines early hiring mistakes with account executives and stresses defining success metrics prior to pilots.
Building Operational Efficiency and Process at Scale 2210 Harry conducts a quickfire round covering process, books, cloud computing, and lessons from Twitter/Airbnb. Florian shares rapid perspectives on edge computing and the essential role of sales in enterprise startups.
Episode Conclusion and Final Advertisements 0000 Harry provides a solo monologue closing the episode and reading sponsor announcements. All host-side and guest dynamic scores are 0 for this non-interactive segment.

Statements from this episode (9)

Insight
Open-source infrastructure tools are powerful but remain difficult to assemble
“I thought that every company should be able to take advantage of a lot of the technology that's out there. It's being released into open source, but that's still really hard to assemble.”
Florian Leibert Jan 19, 2018 ▶ 4:01
Assertion Not checkable as stated
Global 2000 buyers require enterprise procurement rather than self-serve SaaS
“And those companies won't be just putting in a credit card and ordering 500,000 dollars worth of a product on our website. These are contracts that go through long negotiation cycles, they go into procurement, and we got this advice in the beginning many times…”
Florian Leibert Jan 19, 2018 ▶ 5:28
Insight
One-on-one investor advice is more effective than large board meetings
“I think usually I'm a big fan of one-on-one advice, because then you can have a much more honest conversation about everything. It's kind of hard when you're in a room with 10 people or so to really dive in and discuss some really hard issues. I think that's m…”
Florian Leibert Jan 19, 2018 ▶ 6:59
Assertion Supported
HPE resells VMware despite majority ownership by competitor Dell EMC
“And I think if you look at HPE, for example, they also resell VMware, even though VMware is mostly owned by Dell EMC.”
Florian Leibert Jan 19, 2018 ▶ 8:24
Insight
Basing product features on two or three customer interviews fails
“I think if you just talk to two or three customers, you're probably going to end up building the wrong things.”
Florian Leibert Jan 19, 2018 ▶ 13:51
Assertion Supported
Sales represents 40% of expenses at public software infrastructure firms
“If you look at the large public Software infrastructure companies, sales oftentimes makes up 40% or so of their expense”
Florian Leibert Jan 19, 2018 ▶ 15:48
Insight
Establishing shared success criteria before enterprise pilots enables post-pilot sales
“I think it's super important when you go into a pilot, paid or unpaid actually, to identify the success criteria, and if you do that right, You basically can then make a sale upon completion of the pilot.”
Florian Leibert Jan 19, 2018 ▶ 16:28
Assertion Supported
Data volume grows at 40% annually, driving edge computing demand
“So the data is growing at 40% compounded annually, and you just won't be able to just put all of this data into a centralized system.”
Florian Leibert Jan 19, 2018 ▶ 19:12
Insight
Sales execution is as critical as product development for technical founders
“So I came out of engineering, and I never really understood how important sales in a company is. I guess my naive way of going into starting a company in enterprise sales was that if you build a great product, it's going to sell itself. But sales is super impo…”
Florian Leibert Jan 19, 2018 ▶ 20:06
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