May 1, 2020 · 36m · 20vc
20VC: Framework For Hiring The Best Talent 100% Remotely, Raising $32M From Benchmark and GV Pre-Launch and How To Think Through Capital Efficiency and Runway Today with Jeff Seibert and Wayne Chang, Co-Founders @ Digits
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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 repeat co-founders Jeff Seibert and Wayne Chang about their company Digits, detailing their remote-first operational strategy, design philosophy for financial software, and $32M pre-launch capital raising strategy.
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 32.9% of the talking time here. How this is scored →
Harry as informed peer 2.7 Guest teaching 5.0 Guest disagreement 1.3 Harry pushing back 1.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:47 Wayne calls click reduction obsession a 'myopic view'
Wayne directly rejects the premise cited by Harry from DHH and Rahul Vohra, arguing that obsessing over minimizing clicks misses the human element of design.
Hardest push from Harry ▶ 19:18 Harry challenges design strategy using DHH's critiqueHarry uses insights from previous high-profile podcast guests to challenge Wayne on whether modern product managers waste time reducing clicks rather than adding maximalist value.
Biggest teaching moment ▶ 17:16 Jeff educates Harry on top grading interview techniquesAfter Harry confesses he does not know what top grading is, Jeff clearly outlines the structured resume questioning technique that reveals candidate behavioral patterns.
Harry holds his own ▶ 19:18 Harry references industry leaders to test product principlesHarry showcases his industry knowledge by citing DHH and Rahul Vohra to press the guests on product design trade-offs.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Origin Story of Crashlytics and the Birth of Digits | 3 | 4 | 1 | 1 | Harry facilitates the conversation smoothly, asking probing questions about Crashlytics' lessons and tech choices. Jeff and Wayne explain their architectural choices and how they drastically reduced onboarding time compared to traditional competitors. | |
| Framework for Building and Managing Remote Teams | 2 | 5 | 1 | 1 | Harry brings up his own team's struggles with daily remote meetings, prompting Wayne and Jeff to break down their remote work framework. They educate the host on avoiding Zoom fatigue and implementing a two-person buddy system for synchronous work. | |
| Remote Hiring Strategies and Top Grading | 1 | 6 | 0 | 0 | Harry openly admits he does not know what top grading is. Jeff takes the opportunity to explain the formulaic interviewing methodology and how it provides deep signal on candidate performance. | |
| Product Philosophy: Cognitive Load vs. Minimalist Design | 5 | 6 | 4 | 4 | Harry demonstrates industry context by citing opinions from DHH and Rahul Vohra regarding product managers obsessing over reducing click counts. Wayne forcefully pushes back on this premise, arguing that reducing clicks is a myopic view that often sacrifices user context and delight. | |
| Pre-Launch Capital Strategy and Angel Investor Network | 3 | 5 | 1 | 2 | Harry asks why the founders raised $33M pre-launch instead of taking a lean approach. Jeff educates the host on decoupling capital raised from burn rate, explaining that low burn gives Digits over ten years of runway. | |
| Quick Fire Round and Long-Term Vision | 2 | 4 | 1 | 0 | During the quick fire round, Harry asks how VCs can best help founders. Jeff reframes standard VC 'value-add' services, explaining that true value comes from guiding founders on important but non-urgent strategic priorities. |
Statements from this episode (19)
Digits Raised Over $32M From Benchmark, GV, and Angel Founders
“To date, Wayne and Jeff have raised over thirty-two million dollars for Digits, from some of the best in the business, including Peter Fenton at Benchmark, and Jess Verrilli at GV, and then also the most incredible base of angels, with the founders from Box, G…”
Twitter Acquired Crashlytics for Nine Figures Before Selling to Google
“Prior to Digits, Wayne and Jeff co-founded Crashlytics, which was acquired by Twitter for a nine-figure sum in January, and then acquired from Twitter by Google in 2017.”
Crashlytics Reached 300 Million Monthly Active Users Within 12 Months
“Just over 12 months after launch, we hit three hundred million MAUs, and then Twitter acquired us.”
Crashlytics Now Runs on Five Billion Monthly Active Devices
“So, now happy to say that Crashlytics runs on five billion monthly active devices required by Google.”
Corporate Finance Software Competitors Require 16 Weeks to 14 Months Onboarding
“Our competitors, other people that are in the space, they're out there and they're touting that it's so quick to set up. They can get set up in as little as 16 weeks. And that's weeks. That's one of the fastest we found. Others take months or like as little as…”
Back-to-Back Zoom Meetings Destroy Remote Creative Time, Says Wayne Chang
“It's really important that everyone doesn't have just zoom meetings just blocked out throughout the day. That's the worst way to work. That means you're basically replacing The best of remote, which is your ability to form around the objectives, with the worst…”
Digits Averages Five to Seven Minutes for Ad-Hoc Internal Meetings
“We have those three meetings, and then nothing else on the calendar, and everything else is ad hoc, and so I'd say our average meeting length is probably five to seven minutes.”
Paired Buddy Systems Remove the Need for Scheduled Meetings at Digits
“The way this works is we do what's called a buddy system, so every project every week is tackled by two people, some two to four people, but usually two people, and the reason is it's because you're remote, right? Instead of sort of working by yourself in your…”
Digits Requires a Take-Home Work Sample for Every Job Role
“For the skill side, we have used basically a take-home work sample, a take-home challenge that we use for every single role.”
Digits Has Only Fired One Employee Since Its Founding
“We have let one person go in the life of the company, but it's just one.”
Formulaic Resume Questions Easily Reveal Candidate Career Patterns
“And it's just because it's formulaic, And you're asking the same questions for each job role. You can very easily see patterns over a person's career.”
Minimizing User Cognitive Load Often Requires Maximalist Software Design
“When I do the product experiences at Digit and different flows and different things to think about, I'm building product experiences that try to give the users the best experience with the least amount of thinking, the lowest cognitive load. So these result in…”
Crashlytics Raised $6M and Spent Only $3M Before Twitter Acquisition
“So at Crashlytics, we took an incredibly cash-constrained approach, because we were conscious, honestly, of the challenges of the developer tool space. And so for that company, we only ever raised six million in funding. We only ever spent three million of it.…”
Digits Holds Over 10 Years of Runway After Raising $33M
“And so I think the key differentiator here is yes, we've raised thirty three million. We aren't spending it. The big mistake people make is they scale their burn sort of in proportion to their raise. And we haven't. We've kept our team super small and lean. We…”
Startups Should Only Announce News When Prepared to Capture Press Spikes
“So we always advise companies to only do announcements when there's a rational reason for the company to, like, harness the resulting attention of the press. So if you're announcing something just to announce, just so you can see your name in the news, or in t…”
Creative Selection Accurately Depicts Steve Jobs' Apple Product Design Process
“Ken Kosienda's book, Creative Selection, I think it came out a couple years ago or so. My time I spent at Apple actually overlaps with the period he covers in the book, and the book is stunningly accurate in how it portrays how Apple designed and shipped produ…”
A Large Portion of Crashlytics' Original Team Now Works at Digits
“We were very, very thoughtful with how we built the Crashlytics team. And believe it or not, a large portion of that team is now the Digits team, and we're still working together nine years later.”
Digits Took Capital From 72 Angel Investors Spanning 35 Industries
“We ended up with 72, and this gives us 72 different perspectives to build out the product for, and we want to be able to support Different industries, and those 72 represented 35 of the broadest industries that we could find.”
A VC's Greatest Value-Add Is Keeping Founders Focused on Forward-Looking Strategy
“What I think is most helpful is when your investors are always looking forward because they're not caught up in the day to day. And many founders get so caught up in the day to day, their context switching, their racing between fires, that they sort of lose tr…”