Jun 1, 2018 · 29m · 20vc
20VC: Why Every Startup Will Either Fail or Rebrand, How To Do OKRs The Right Way & How To Know The Reversible From the Irreversible Mistakes with Jack Groetzinger, Founder & CEO @ SeatGeek
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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 VC, host Harry Stebbings interviews SeatGeek Founder and CEO Jack Groetzinger about building and scaling a premier ticketing platform. Groetzinger shares operational insights on organizational alignment through OKRs, engineering recruitment, venture fundraising evolution, board dynamics, and executing strategic acquisitions.
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 38.3% of the talking time here. How this is scored →
Harry as informed peer 3.0 Guest teaching 2.3 Guest disagreement 1.1 Harry pushing back 1.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 24:06 Defending morning routine
Jack playfully defends himself against Harry's question about sleeping on a sofa and eating 15 egg whites, noting that 15 egg whites is not actually that many.
Hardest push from Harry ▶ 5:58 Challenging board intervention on blind spotsHarry presses Jack on why his board didn't step in earlier to rectify the lack of a finance hire if that was an obvious blind spot.
Biggest teaching moment ▶ 4:23 Debunking technical vs commercial skill dynamicsJack reframes Harry's question on founder skill sets by explaining that technical skills are fundamental while commercial execution is easily learned on the job.
Harry holds his own ▶ 14:46 Detailing customer acquisition channel decayHarry showcases informed expertise by highlighting the mortality of customer acquisition channels over time as costs increase.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Origin Story of SeatGeek | 3 | 3 | 1 | 2 | Harry uses investor-sourced questions to prompt Jack on founder skill sets and early hiring oversights. Jack reframes the tech versus commercial debate and explains board dynamics. Harry offers mild pushback on why the board didn't interject sooner regarding finance hires. | |
| Implementing OKRs and Scaling Company Alignment | 2 | 2 | 1 | 1 | Harry asks standard operational questions about OKR implementation and company culture at scale. Jack explains Andy Grove's OKR framework and targeting a 70% achievement rate without friction. | |
| Engineering Recruitment and Employer Branding Strategy | 3 | 2 | 1 | 1 | Harry asks about engineering recruitment strategies based on investor notes. Jack details treating recruitment like a funnel and investing in employer brand building. | |
| Fundraising Evolution and Customer Acquisition Economics | 5 | 3 | 1 | 2 | Harry demonstrates strong domain understanding by bringing up channel decay and customer acquisition costs being bid up by incumbents. Jack articulates how repeat usage offsets acquisition costs. | |
| Board Value, Friction, and Reversible Decisions | 3 | 2 | 1 | 2 | Harry explores investor empathy and board friction, as well as New York tech ecosystem dynamics. Jack elaborates on reversible versus irreversible decisions. | |
| Executing Major Acquisitions: The TopTix Story | 2 | 2 | 1 | 1 | Harry asks about the TopTix acquisition. Jack explains the culture risks and integration process when doubling company size. | |
| Strategic Hindsight on Growth and Aggression | 3 | 2 | 2 | 2 | In the quickfire round, Harry asks rapid-fire questions on branding, competition, and habits. Jack lightheartedly corrects Harry's framing regarding his morning routine and egg whites consumption. |
Statements from this episode (15)
Ticket buyers wanted actionable recommendations over raw data
“Pretty early on, we realized, thanks to user feedback, that people didn't just want data. They actually wanted us to help them suggest what tickets to buy and sort of push them through that process.”
Technical skill is the most important factor for startup founders
“Being technical is far and away the most important criterion that sort of drives success. Basically, you can't have too many technical people On a founding team.”
SeatGeek raised nearly $100M before hiring its first finance employee
“We waited forever to hire a full-time finance person. I think we'd raised almost a hundred million dollars before we hired anyone full-time in finance”
Board seats are immutable commitments requiring extensive founder diligence
“When you agree to take someone out of your board and raise a bunch of money from someone, just how long-term sort of immutable the commitment is. I think if a lot of founders realized that fully, they would do more work and more diligence and spend more, more …”
Achieving 100% of OKRs indicates sandbagging and conservative goal-setting
“If you're doing it right, then on average, you're averaging about 70% accomplishment as a company. And if you're getting close to a hundred, it means that you're really sandbagging and that you're not setting aggressive enough goals.”
Blogging and open-sourcing code act as force multipliers in recruiting
“I think people tend to be a little bit myopic and not invest in sort of employer brand building stuff that can actually be really impactful. So, you know, a few examples of that are blogging about the things that you're doing, open sourcing software, Both of t…”
SeatGeek acquired TopTix for $56M using an equal-sized funding round
“So we acquired a company called Toptics. For fifty six million dollars last year, and we raised a, around, it was almost exactly that amount to finance the deal.”
Twitter fell from SeatGeek's top acquisition channel to tenth
“For us, for example, the channel that was our very biggest driver back in 2013, Twitter, mobile acquisition has become probably number 10 on the list right now.”
Startups face at most two or three major strategic decisions yearly
“Each company maybe has two to three sort of major strategic moments per year at most, but they're incredibly important to get right and can be company champion.”
SeatGeek can realistically be NYC's top employer brand, unlike in SF
“If we want to build a differentiated brand as we want to be the best place for an engineer to work in New York, that would be sort of a ludicrous, probably overambitious thing for us to say if we were based in San Francisco. There's just so many iconic technol…”
Lack of major liquidity events constrains the New York tech ecosystem
“The challenge, of course, the flip side of that is just the total pool of people is smaller. Even more specifically, there haven't been that many really big liquidity events, you know, sort of Google-style companies. Equity events that spin off a bunch of peop…”
SeatGeek prefers PhDs and quant traders over bootcamp data science grads
“The biggest challenge sort of sorting through the data science pool is filtering the people who are sort of very serious quantitative professionals versus folks who did a boot camp. For three months and are now trying to become a data scientist. And there's ab…”
SeatGeek delayed fundraising until unit economics proved highly favorable
“We waited a long time to raise money until we were really sort of irrefutable and controvertible evidence that the CAC LTV math was heavily in our favor and would be idiots not to raise more money.”