Sep 21, 2022 · 1h 8m · news
David Lieb: How I Founded Google Photos & Bump; Why I Left Google | 20VC #927 · 20VC with Harry Stebbings
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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 interview, tech entrepreneur and former Google Photos lead David Lieb discusses his journey from founding Bump to scaling Google Photos, sharing his deep product management frameworks, hiring philosophies, and personal reflections on resilience and startup investing.
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 19.4% of the talking time here. How this is scored →
Harry as informed peer 3.9 Guest teaching 3.8 Guest disagreement 1.1 Harry pushing back 1.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:01:40 Reframing developer founder charisma
David explicitly rejects Harry's assertion that developer tool founders lack charisma, explaining that credibility with technical peers is what constitutes charisma in that domain.
Hardest push from Harry ▶ 1:01:35 Challenging uncharismatic technical foundersHarry forcefully challenges David's emphasis on charisma by arguing that devtool founders often have 'the charisma of a lemon' and expresses concern about missing great investments.
Biggest teaching moment ▶ 17:30 Gut instinct as the ultimate machine learning modelDavid educates Harry on product intuition by reframing human gut instinct as an extraordinarily trained, multi-generational supercomputer that beat-for-beat outperforms simple data analytics.
Harry holds his own ▶ 26:50 Pressing on 30-day retention benchmarksHarry asserts his VC perspective by pushing back on generic retention graphs and referencing Jeremy Liu's 36% 30-day retention benchmark for Snapchat.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| David Lieb's Accidental Path to Tech Entrepreneurship | 1 | 2 | 0 | 0 | Harry opens with an enthusiastic intro question about David's transition into tech and Google. David casually explains his accidental path from Texas Instruments and business school to launching Bump and Y Combinator. | |
| Crucial Lessons: The Power of Startup Ownership Mentality | 3 | 4 | 1 | 1 | Harry shares his own personal struggles with delegating sales and asks how founders should determine product-market fit. David offers a clean reframe, noting that if a founder is unsure whether they have PMF, they don't. | |
| Deciding to Sell: Managing Growth Constraints and the Visual Data Explosion | 2 | 3 | 0 | 0 | Harry asks why David sold Bump and what drove Google Photos' success. David articulates the core insight regarding the explosion of photo data and the necessity of establishing a focused mission early on. | |
| Personal Trials: Surviving Leukemia and Transitioning to Y Combinator | 1 | 3 | 0 | 0 | Harry respectfully asks David about his decision to leave Google. David shares his personal battle with leukemia and how the near-death experience prompted his transition to Y Combinator. | |
| Product as Art: The Power of Gut Instinct and Embracing Variance | 4 | 5 | 2 | 3 | Harry probes whether product development is art or science and questions downside protection when relying on gut instinct. David delivers a powerful counter-perspective by describing human gut instinct as the ultimate machine learning model. | |
| Shipping with Intention: Balancing Day-One Quality with Iterative Speed | 6 | 4 | 1 | 3 | Harry demonstrates strong venture knowledge by questioning 30-day cohort retention curves and citing Jeremy Liu's benchmark for Snap. David balances this by explaining how macro metrics can mislead, sharing an anecdote where 20% of Bump opens were accidental taps. | |
| Team Building: Holistic Ownership, Modeling Culture, and the CPO Trap | 5 | 4 | 1 | 2 | Harry cites Calendly CPO Annie Pearl regarding founder missteps when hiring CPOs. David confirms the premise and candidly shares his own past mistake of hiring a product lead prematurely at Bump. | |
| Product Leadership Archetypes: Visionaries, Craftsmen, and Operators | 6 | 4 | 1 | 3 | Harry uses Shreyas Doshi's product framework to critique process-obsessed 'operator' CPOs who add little value. David agrees wholeheartedly and discusses why non-traditional hires often outpace experienced median product managers. | |
| Product Reviews and Driving Accountability Through DRIs | 4 | 4 | 1 | 2 | Harry asks detailed operational questions about conducting effective product reviews and managing remote work dynamics. David explains Apple's DRI model and reveals his tactic of arriving late to Zoom calls to spark informal culture building. | |
| Angel Investing: Backing High-Conviction Founders and Static Check Sizes | 6 | 4 | 2 | 3 | Harry engages in VC peer talk about institutional check sizing versus angel investing flexibilities. David explains why he keeps check sizes static to avoid misjudging non-obvious breakout hits like Flexport. | |
| Redefining Charisma: Storytelling vs. Engineering Authenticity | 5 | 5 | 3 | 4 | Harry forcefully challenges the charisma of technical/devtool founders, claiming they have 'the charisma of a lemon.' David rejects the premise, reframing charisma as domain-dependent and relative to the target audience. |
Statements from this episode (27)
Lieb: Bump pivoted to photo sharing before being acquired by Google
“We pivoted a few times with bump and ultimately decided to work on photo sharing and then got acquired by Google. And then I was there for nine years.”
David Lieb: Concentrating generalist skills in few people yields extraordinary results
“And I think that's a skill, this like generalist skill that generally people don't have at big companies because they don't need to. There's experts at big companies that do everything, but I think magic happens when you bring all that stuff together in a very…”
Lieb: Founders delegate sales and core roles too early
“You certainly need to make that trade off at some point, but I think most founders do it too early. They think they think like, oh, we have a product that like shows some glimmers of, you know, product market fit. Let's go hire a sales team. And that will be t…”
Lieb: If you are unsure about product-market fit, you lack it
“If you don't know if you've got it or not, you don't is the simplest answer, right? It is a thing where something clicks and people just use your product or demand your product so much more than you could have ever fathomed. That is generally when you've got s…”
Lieb: Bump sold to Google because it needed to raise capital
“We need, we were gonna need to raise some more money and we weren't sure that that was the right idea for ourselves or for the team or for investors. So usually when you sell a company, it's because you either really can and want to or you need to. For us, we …”
Lieb: Google Photos intentionally rejected social features and photo editing
“And we said internally at Google, like, we're not going to build a social tool. This isn't a social network. Like, that's not what we're doing. We're not going to build some crazy, like, photo editing product. Like, it's not about being, quote, creative with y…”
Lieb: Google Photos team was originally spun out of Google+
“There were a bunch of people that were on the existing, we kind of spun the team out of the Google Plus team, and there were a bunch of folks who signed up to build social, right? They were very excited about social, and that's awesome, but we were very clear,…”
Lieb: Great products are always built by tiny, obsessed teams
“If you look at like truly great products, pick any product that you use that you're like, that product is just really well done. Generally there are a very small set of people behind that product That really love it. That obsess over every single thing about i…”
Lieb: Analytical product design prevents failure but caps upside
“Using science kind of bounds your variance of your outcomes. It makes sure you don't, like, totally blow it, but it also makes sure that you don't, like, find something that no one else would have found because you would never try it. And that's where I think …”
Lieb: Human gut instinct is the ultimate machine learning model
“I think your gut is the world's most sophisticated machine learning model ever created. It is like the best supercomputer we've got.”
Lieb: Startups should ship early to learn, while big companies need polished launches
“For most startups, the answer is you should probably ship something and learn something from someone. And then you can make it better. If you're a big company, you might need to make something like quite good before you want to launch it.”
Lieb: Cohort retention is the single most important early product metric
“I think that's the number one thing you should look at when you're building a new product is what is your cohort retention curve look like?”
Lieb: Bump reached 150 million installs, on 20% of global smartphones
“In, in, in the Bump kind of heyday, we had a hundred and fifty million installs on, on phones when the market for phones was only like, I don't know, maybe a billion phones in the world, or probably less than that, probably hundreds of high hundreds of million…”
Lieb: 20% of Bump app opens were accidental taps meant for Facebook
“We thought we were like hot shit because everybody's using our app, but turns out like 20% of the time it was accident. They didn't mean to use it.”
Lieb: Early-stage startups shouldn't scale teams before finding product-market fit
“This is another meta mistake is people think like, oh, I like, I've raised my seed round. I have four million dollars. Like, let's go hire a team of 20 people. That's what I see all my cohorts cohort members doing. That's probably the wrong thing to do unless …”
Lieb: Ambition is the single most important trait when hiring early PMs
“I would say at the early stage, the number one thing I would filter for initially for product people, and product people at an early stage company is a very broad set of skills. Like, you're kind of looking for people who can kind of do anything decently well.…”
Lieb: Prematurely hiring a product lead at Bump was a key mistake
“At bump, you know, we got to like, Maybe it was 30 employees, and we were, all of our vanity metric graphs were, like, going way up. We were feeling really good and I thought, oh, like, our company is gonna need to, like, figure out our business model eventual…”
Lieb: Over-indexing on scale or tenure is top product hiring mistake
“I would say like the number one failure mode when people hire product leaders is they over index on Either like previous scale, like how many, how big of a team have you previously managed? Or tenure, like how long have you been doing this? What experience do …”
Lieb: Hiring a B-player product leader destroys top team talent
“It happens, like, literally all the time. I watch it happen, and once you hire that B player to be your lead, like, bye-bye. Your team is gone. Like, the best people on your team are not gonna wanna work with that person.”
Lieb: Prior domain experience is anti-correlated with top product performance
“In my experience, most of the really strong PMs that have emerged, say on the Google Photos team came from backgrounds with no experience in this domain really at all. Like you talked to some of them. In fact, I would say, I would probably go so far as to say …”
Lieb: Joining remote meetings late intentionally builds team culture
“The technique that I found, like, the most successful, it's the simplest thing I could think of, is for every meeting that I was kind of, like, the top person in, I would just intentionally show up, like, five to seven minutes late. And I would, it creates thi…”
Lieb: Modulating angel check sizes by success probability is counterproductive
“So if you modulate your check size based on like probability of success or like how big the market is or whatever, you'll probably be doing the exact opposite of what you should do.”
Stebbings: Developer tool founders are often extremely uncharismatic
“When you look at the next generation of founders, often building developer tools, API economy, respectfully, they have the charisma of a lemon or a pineapple, I mean, they are the most uncharismatic people in the world”
Lieb: Founder charisma is relative to target recruits
“What some people might call like very non-charismatic or uncharismatic, but be like very charismatic to the group of people you want to hire.”
Lieb: I was asked to leave my Google team twice
“I didn't get fired from Google. I did get asked to leave the team twice.”
Lieb: Product managers should oversee design, engineering, and analytics
“I think the product manager role as defined by the world is way too pigeonholed. I think we should broaden the responsibilities of the PM role. I think they should be much more responsible for design, much more responsible for engineering, for analytics. Like,…”
Shorts cut from this episode
▶ POV: Your app has 150 million installs · 20VC with Harry Ste (@28:33)
▶ What makes a good user retention rate? — David Lieb (the cre (@29:54)
▶ POV: Your app has over 150 MILLION installs 📈😲 #shorts · 2 (@28:33)
▶ What I learned from creating a startup #shorts · 20VC with H (@2:29)
▶ How I turned $10k into MILLIONS 💰🚀 #shorts · 20VC with Har (@59:57)
▶ What is a good Customer Retention Rate? 📊 #shorts · 20VC wi (@29:54)