Feb 10, 2022 · 20m · top-founders
Digits Wants to Replace Quickbooks, $30m Raised, 4 years of Building Distribution, Launch is Next
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, serial entrepreneur Jeff Seibert discusses his entrepreneurial journey from founding and selling Increo and Crashlytics to building Digits, a real-time small business finance platform backed by $30 million in venture funding and 72 prominent angel investors.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 39.1% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Jeff bluntly pushes back on Nathan's public estimate that Crashlytics was acquired for $38M, stating the actual transaction was well over $100M.
Hardest push from Nathan ▶ 13:42 Host challenges incumbent moat in accountingNathan directly challenges Digits' value proposition by questioning why massive incumbents like QuickBooks and FreshBooks haven't already built real-time workflows.
Biggest teaching moment ▶ 7:55 Jeff sets the record straight on exit valuationJeff clarifies the actual scale of the Crashlytics acquisition to over $100M after Nathan recites inaccurate public transaction figures.
Nathan holds their own ▶ 2:30 Nathan lays out dilution math vs bootstrappingNathan shows sharp SaaS financial fluency by calculating founder equity dilution sub-5% over long VC cycles versus keeping 100% of a bootstrapped business.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Introducing Jeff Seibert and The Social Dilemma | 5 | 2 | 1 | 2 | Nathan analyzes Aaron Levie's heavy dilution down to under 5% at IPO versus the financial upside of bootstrapping a $15M-$20M business. Jeff agrees that bootstrapping is much more viable today than when Box started. | |
| Engineering Management at Box and Genesis of Crashlytics | 5 | 1 | 0 | 1 | Jeff recounts negotiating IP ownership while at Box to build Crashlytics and raising a seed round in Boston. Nathan demonstrates market familiarity by accurately predicting the 1 on 5 valuation cap. | |
| Scaling to 300 Million Devices and Twitter Acquisition | 3 | 6 | 2 | 2 | Jeff explains reaching 300 million devices in 12 months with zero revenue. When Nathan asserts Twitter acquired Crashlytics for around $38M, Jeff corrects him that the sale was well over $100M. | |
| Twitter Product Leadership and Climate Documentaries | 2 | 1 | 0 | 1 | Jeff shares his involvement as an executive producer and participant in climate and tech documentaries like The Social Dilemma. Nathan inserts a mid-roll advertisement for Founderpath valuation software. | |
| Digits: Disrupting Small Business Finance with Real-Time Data | 5 | 4 | 1 | 4 | Jeff details Digits' thesis on real-time financial reporting versus delayed monthly book closes and building built-in virality. Nathan challenges Jeff on why incumbents like QuickBooks and FreshBooks haven't solved this. | |
| Raising $30M+ Pre-Revenue and Pitching Long-Term Vision | 5 | 3 | 1 | 3 | Nathan inquires how Digits raised over $30M pre-revenue from Benchmark and GV while keeping dilution reasonable. Jeff outlines how pitching massive market TAM and founder track record enables top-tier valuations without current metrics. | |
| Orchestrating a 72-Person Angel Party Round | 4 | 2 | 1 | 3 | Nathan explores the 72-person angel round and asks why Jeff didn't recruit accounting firms directly for distribution leverage. The conversation concludes with standard Famous Five lightning round questions. |