May 8, 2020 · 28m · 20vc
20VC: How Roam Research Analyse Product Design, Team-Building, The Future of Collaboration Tools & Applying Tesla Go-To-Market To Roam with Conor White-Sullivan, Founder & CEO @ Roam Research
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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 20VC, host Harry Stebbings speaks with Conor White-Sullivan, co-founder and CEO of Roam Research, about building networked productivity tools, lessons in grit from high school wrestling, hiring autodidacts, and executing a Tesla-inspired go-to-market 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 29.8% of the talking time here. How this is scored →
Harry as informed peer 3.4 Guest teaching 3.4 Guest disagreement 3.1 Harry pushing back 1.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 21:50 Dismissing the Question Premise
Connor flatly rejects Harry's bundling vs unbundling question framing, responding with 'moo' and calling it 'in some ways, the wrong question'.
Hardest push from Harry ▶ 23:14 Self-Deprecating Counter-PushbackAfter Connor dismantles his question framing, Harry acknowledges the critique immediately, exclaiming 'What a shit question. Terrible question.'
Biggest teaching moment ▶ 22:00 Graph vs. SQL Database ParadigmsConnor educates Harry on why traditional SQL tables fail for relational thought, arguing that graph databases represent true connections between thoughts and projects.
Harry holds his own ▶ 20:16 Reframing Roam Against GoogleHarry shows deep understanding of Roam's scope by asking if Google is a more accurate comparison than traditional note-taking apps.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Lessons from High School Wrestling and Learning to Win | 3 | 2 | 1 | 1 | Harry asks Connor to connect his high school wrestling grit to advice for founders balancing vision versus knowing when to pivot. Connor reflects on learning to win after losing for years and balancing tactical agility with long-term faith. The tone is reflective and collaborative. | |
| The Origins of Roam Research and Collective Intelligence | 2 | 3 | 2 | 1 | Connor reframes Roam Research from a simple note-taking application to a mechanism for collective intelligence and compound interest on thoughts. Harry prompts with personal context about law school. Connor outlines how Roam helps users collaborate with their past and future selves. | |
| Designing Product Learning Curves: Low Floor, High Ceiling | 6 | 4 | 2 | 2 | Harry demonstrates strong podcast context by citing Rahul Vohra from Superhuman to ask about designing product challenge and learning curves. Connor explains the Excel philosophy of low floor and high ceiling, advocating for steep learning curves for power users. Harry pushes on whether Roam considered white-glove onboarding like Superhuman. | |
| Building a Cult Community and Challenging Existing Paradigms | 4 | 5 | 6 | 2 | Connor exhibits strong contrarian views, attacking Evernote as an outdated second brain and critiquing file-folder paradigms. Harry validates Connor's stance by observing that divisive mission statements create strong cult communities. Connor highlights his Twitter battles with productivity figures like Tiago Forte. | |
| Applying Tesla's Go-To-Market Strategy to Roam | 3 | 5 | 5 | 1 | Connor details his Tesla-inspired go-to-market strategy, starting with elite power users like AI safety researchers to fund product maturity. He explicitly contrasts Roam with Notion's strategy of appealing to the lowest common denominator. Harry listens and allows Connor to elaborate on organic testimonial growth. | |
| Hiring Philosophy: Autodidacts, Grit, and Ecole 42 | 2 | 2 | 2 | 1 | Harry asks Connor about his hiring philosophy regarding grit and autodidacts. Connor shares the story of finding his co-founder at Ecole 42, describing the intense multi-hour logic testing and high attrition rate that filtered for self-directed learners. | |
| Company Culture and Living with the Team | 5 | 4 | 3 | 2 | Harry elevates the interview by proposing that Google is a truer competitor to Roam than standard note apps like Notion or Evernote. Connor validates Harry's comparison, explaining that Google organizes information for advertising whereas Roam builds a read-write web for human knowledge graphs. | |
| Bundling vs. Unbundling and Graph Databases | 4 | 6 | 7 | 3 | Connor forcefully rejects Harry's question on bundling versus unbundling, calling it the wrong framework and opting for a graph database paradigm instead. Harry humorously concedes that his question was terrible before transitioning to quickfire rounds where Connor also calls venture capital black swan farming claims bullshit. | |
| Interview Conclusion and Final Thoughts | 2 | 0 | 0 | 0 | The interview concludes with mutual appreciation. Connor compliments Harry as an ideal power user of Roam, and Harry signs off with sponsor announcements. |
Statements from this episode (20)
20VC uses Roam Research for all episode preparation
“We actually structure all of our thinking and preparation for every show using Rome behind the scenes”
White-Sullivan: Believing Problems Are Solvable Primes Founders to Spot Opportunities
“Yeah, figuring out how to maintain faith in yourself, and maintain faith in your ability to eventually solve the problems that are not solvable or tractable to today, but figure out how to make progress, and it's interesting, because I'm sort of a believer in …”
White-Sullivan: Writing enables compound interest on human thought
“Writing is a tool for thinking, and if you can't get compound interest on your thoughts, if you can't build up a thought structure over time and continually go back and revisit it and revise it, you're limited to just what you can hold in your head.”
White-Sullivan: Rephrasing insights in own words crystallizes learning
“Write down some of the core insights in your own words. Just that action alone is going to crystallize the thought, test your understanding of it, and help you remember it later.”
White-Sullivan: Roam's long-term goal is shared belief architecture
“The long-term goal, right, is being able to do that also with other people, being able to build off of other people's belief architecture or other people's evidence that they found for certain things.”
White-Sullivan: Roam Research's Product Role Model Is Microsoft Excel
“Our role model for this is Excel.”
White-Sullivan: Steep Product Learning Curves Accelerate User Mastery
“A steep learning curve is a good thing, because if the mountain is steep, then it takes actually a relatively short amount of time to get to the top of it.”
Roam Research Required User Onboarding Calls and Free Access at Launch
“When we first launched, we did require every person who came in to go through a onboarding call, but we weren't charging from the first day because actually we wanted to be able to lean on end user innovation and see how people were using it.”
Conor White-Sullivan Spends Nine Hours Every Tuesday on User Calls
“I still do every Tuesday, basically from 10 a.m. To seven p.m. I'm on user calls. So I'll do a lot of 30 minute onboardings.”
White-Sullivan: Evernote is a terrible tool for research and organizing ideas
“Evernote is a terrible second brain and just not a good place for organizing your ideas or building up a repository of research.”
White-Sullivan: Evernote's file-and-folder architecture creates unnecessary friction
“Evernote's not built the way your brain is, and a lot of the friction that you have with reusing thoughts in Evernote is Incidental complexity, because they follow this files and folder metaphor from an archaic time”
Roam Research funded its first two years via AI safety enterprise contracts
“We actually got off the ground by getting customer funding from some folks in the effective altruist and particularly the AI safety community, people who are thinking about AI risk, and I would say like the broader Bay Area rationalist community, and so people…”
White-Sullivan: Notion caters to the lowest common denominator of users
“Their approach is like, it's got to be really intuitive for every user who comes in. Let's play to the lowest common denominator. You shouldn't really have to change your way of thinking to use Notion.”
White-Sullivan hired co-founder Joshua Brown after Brown learned Clojure in 3 weeks
“If you can teach yourself closure in a month, I'll give you a job. And he learned it in three weeks and then made him an offer to be a co-founder, like maybe three or four weeks after that.”
White-Sullivan is building Roam so his children will not need school
“I want to build this graph of the world's knowledge so that my kids don't ever have to go to school.”
Conor White-Sullivan: Google prioritizes user tracking for ad serving over organizing knowledge
“Google set out to organize the world's information, and now they are organizing all the information about their users to serve the perfect ad, which is not the same thing.”
White-Sullivan: Graph databases represent relationships between thoughts better than SQL
“We're so bullish on graph databases, is that they're a better representation for the relationship between thoughts, the relationship between projects, the relationship between people, and yeah, most of the tools that we have out there are based on the SQL data…”
White-Sullivan: VC rhetoric on 'black swan farming' is largely bullshit
“I think that for all the talk of black swan farming, a lot of it's really bullshit. I mean, it's been amazing to me how many people want to invest in Rome now versus how few wanted to a year ago when, like, 10,000 dollars would have made the world of differenc…”
Richard Meadows was the first investor in Roam Research
“First check was a guy named Richard Meadows, who's famous for eating only pizza for a year... He played with a very early prototype that I had, And he was the first Czech into Rome, and he's a great friend, and helped us write the white paper later”