Jan 29, 2016 · 28m · 20vc
20 VC FF 032: Jeff Seibert on Lessons From Being Acquired By Twitter & Box and Now Leading Twitter's Consumer Product
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews serial entrepreneur and Twitter Senior Director of Product Jeff Seibert about his journey from childhood coding to founding InCrayo and Crashlytics, offering strategic advice on fundraising, acquisitions, team leadership, and product scale.
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 21.6% of the talking time here. How this is scored →
Harry as informed peer 2.6 Guest teaching 3.1 Guest disagreement 0.6 Harry pushing back 2.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 7:24 Gently rejecting host's desperate runway premise
Jeff explicitly clarifies that six months was standard timing rather than a desperate mistake, distinguishing between fundraising timeline norms and the delay in seeking strategic alternatives.
Hardest push from Harry ▶ 7:07 Challenging startup timing and positionHarry directly questions whether Jeff waited too long and put his team in a desperate situation when approaching VCs on Sandhill Road during the 2009 downturn.
Biggest teaching moment ▶ 9:44 Masterclass on CEO emotional dampingJeff articulates a deep operational thesis explaining why excessive transparency causes organizational paralysis during acquisition talks and why a founder must absorb company highs and lows.
Harry holds his own ▶ 9:27 Citing Ben Horowitz on workplace transparencyHarry uses Ben Horowitz's well-known philosophy on transparency to challenge Jeff's assertion that founders should withhold acquisition details from their staff.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Jeff Seibert's Origin Story and Early Coding Discovery | 1 | 2 | 0 | 0 | Harry offers warm introductory prompts asking for Jeff's backstory and the origin of InCreo. Jeff recounts his childhood discovery of Mac programming in Baltimore and his Stanford background in an agreeable, narrative tone. | |
| Navigating Startup Fundraising During the 2009 Financial Crisis | 3 | 3 | 1 | 5 | Harry presses Jeff on whether leaving six months of runway put the company in a desperate position during the 2009 financial crisis. Jeff gently reframes the issue, explaining that six months was standard for fundraising, but their mistake was delaying alternate pivot options. | |
| Managing Organizational Transparency and Mission Alignment in Acquisitions | 4 | 5 | 1 | 4 | Harry invokes tech industry gospel from Ben Horowitz favoring total transparency to challenge Jeff's view. Jeff provides a compelling response on how founder transparency during M&A talks can paralyze product engineering teams. | |
| The Crashlytics Growth Story and Strategic Acquisition by Twitter | 3 | 4 | 1 | 3 | Harry probes why Crashlytics sold to Twitter despite strong standalone growth and available funding. Jeff educates Harry on Twitter's strategic vision for mobile SDK consolidation and how deal terms guaranteed ongoing headcount investment. | |
| Boston Startup Ecosystem and Partnering with Co-Founder Wayne Chang | 3 | 2 | 0 | 0 | Harry brings in a tailored question from Flybridge investor Jeff Bussgang regarding how Jeff selected co-founder Wayne Chang. Jeff shares how Wayne proved his execution capability by securing user feedback from top media executives before officially joining. | |
| Overcoming Post-Acquisition Pitfalls and Achieving Scale | 3 | 4 | 1 | 3 | Harry notes Jeff's past comment regarding post-acquisition organizational reorgs and asks how founders can secure access to key executives. Jeff details how unexpected corporate reorgs occur and advises negotiating fixed six-to-nine-month reporting commitments. | |
| Leading Consumer Product and Corporate Culture at Twitter | 1 | 2 | 0 | 0 | Harry asks standard operational questions regarding post-acquisition life at Twitter and future plans. Jeff outlines Twitter's low employee turnover after the acquisition and his role leading the internal 'Bluebird' consumer product team. |
Statements from this episode (14)
Harry Stebbings: Twitter acquired Crashlytics for $259M
“Which I believe is used on over a billion devices today, and they were ultimately acquired for two hundred and fifty nine million dollars by Twitter.”
Stebbings: Box's first-ever acquisition was InCrayo in 2009
“Before Crashlytics, Jeff was the founder of InCrayo, which was Box's first ever acquisition in 2009.”
Seibert: Entrepreneurs shouldn't wait for a mind-blowing, perfect idea
“And I think that was the first big lesson I learned is not to sort of hold out for this perfect concept that's going to blow the world away. Very, very few businesses start out as this like mind blowing idea that no one's ever thought of.”
Seibert: The average startup fundraising round takes four to six months
“And if you look on the, at the data, the average round takes six to four to six months to close.”
Seibert: Dual-tracking M&A and funding yields stronger acquisition deal terms
“If we had started in January and had a full six months to sort of side by side pursue funding and partnerships or acquisition, I think we would have been in a much stronger position.”
Seibert: Radical transparency during M&A talks paralyzed InCrayo for two months
“So for the two, two and a half months that we were going through these acquisition discussions, we built basically nothing.”
Seibert: Founders must dampen startup volatility to keep teams productive
“And I think in retrospect, it's your job as the founder to really dampen this roller coaster for your team so that they can remain productive and give your team a really set direction that they feel comfortable and confident executing on.”
Seibert: Acquisitions are about mission acceleration, not cashing out
“My belief on acquisitions and IPOs for that matter, exits of any kind is that they are not about exiting. The entire point is to become more successful at your mission.”
Seibert: Twitter made Crashlytics free and expanded the team to launch Fabric
“And so they were willing to make Crashlytics free. They were willing to help us grow our team significantly so that we could build adjacent products, which we ultimately did and became a suite known as fabric.”
Seibert: Twitter acquires an average of one to two companies a month
“Twitter on average acquires one to two companies a month. They have for years.”
Seibert: Acquired founders should negotiate 6-to-9-month reporting commitments
“What I would have done in retrospect is sought some commitment to continue to report to that person for X period of time. I don't think it's fair or actually good to say, Hey, I want to indefinitely report to this person. You want to move around as the company…”
Seibert: Crashlytics is installed on substantially every active mobile device on Earth
“So today Crashlytics is installed on well, well over a billion devices. We're on substantially every active mobile device on earth.”
Seibert: Crashlytics team tripled at Twitter with only one employee resignation
“Our team had not only has tripled, but only one person has left in that time.”
Jeff Seibert: Acqui-hires are bad from a startup perspective
“Not a fan. In they're pretty good from the larger company's perspective, because you get a team for a relatively low price that you know works well together. And that you can't undervalue. From the startup side, I'm not a fan because I'm, I deeply believe in s…”