Sep 29, 2017 · 26m · 20vc
20VC: If You Do Not Like VCs, You Have Not Worked With a Good One, How Andreesen Have Added The Same Level of Value As A Co-Founder, Why Market Is The First Thing To Consider When Angel Investing & Why Series A Is A Hiring Decision with Roger Dickey, Foun
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In this episode of The 20 Minute VC, host Harry Stebbings interviews Roger Dickey, founder and CEO of Gigster and creator of Mafia Wars. Dickey discusses his rapid prototyping methodology, the scaling of managed software marketplaces, venture capital partnerships, and his strategic framework for angel 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 29.4% of the talking time here. How this is scored →
Harry as informed peer 2.3 Guest teaching 2.8 Guest disagreement 0.7 Harry pushing back 0.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:30 Rejecting team-first VC consensus
Roger explicitly counters the ubiquitous Silicon Valley belief that team always comes first, arguing that market is the primary criteria for startup success.
Hardest push from Harry ▶ 14:20 Challenging market-first evaluation on market creationHarry pushes back on Roger's market-first stance by questioning how one evaluates market size when novel technologies shift and create new markets entirely.
Biggest teaching moment ▶ 11:40 Deconstructing Series A VC evaluation processRoger educates Harry on how top firms like Sequoia evaluate Series A rounds as hiring decisions rather than purely inspecting current business metrics.
Harry holds his own ▶ 22:02 Citing Elad Gill on deep tech vs clean tech bubbleHarry demonstrates deep industry knowledge by citing Elad Gill's specific historical comparison between contemporary deep tech hype and the 2000-2003 green tech bubble.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Testing Ideas and Rapid Prototyping Before Gigster | 1 | 2 | 0 | 0 | Harry asks a straightforward introductory question about Roger's rapid prototyping process. Roger explains testing over 20 ideas before Gigster and how simple landing pages were used to gauge interest. | |
| Early Demand Validation and Launching Gigster | 2 | 3 | 1 | 1 | Harry introduces a quote from Naval Ravikant regarding self-employment trends. Roger provides nuance on customer validation, explaining that payment is not always the immediate first metric for freemium or complex platform models. | |
| Scaling Business Model and Handling Complex Projects | 2 | 3 | 0 | 0 | Harry quotes Roger's tweet regarding VCs to prompt a discussion on investor value-add. Roger outlines how Andreessen Horowitz's operating partner model functions like a true co-founder. | |
| Series A Fundraising Dynamics and Founder Backing | 3 | 4 | 2 | 2 | Roger gently rejects the traditional VC dogma of 'always back the founder first,' arguing that market dynamics precede founder quality. Harry pushes back by asking how market creation and transience impact that assessment. | |
| Balancing Angel Investing with CEO Responsibilities | 3 | 3 | 0 | 0 | Harry probes into personal finance and LP portfolio allocation models. Roger breaks down his shift to reactive angel investing and the realities of illiquidity in venture capital. | |
| Quick Fire Round: Technology, Productivity, and Deep Tech | 3 | 2 | 1 | 0 | Harry cites Elad Gill's comparison between deep tech investing and the early 2000s clean tech bubble. Roger agrees with the framing and expands on hype-driven seed investing. |
Statements from this episode (17)
Roger Dickey helped build Mafia Wars to $1B revenue and 100M users
“Prior to Gigster, Roger founded Mafia Wars, where he helped build the business to one billion in revenue and a hundred million users.”
Roger Dickey tested 25 business ideas before launching Gigster
“Before Gigster, we actually tried about 25 different ideas. We built prototypes, shipped them on Product Hunt or Hacker News.”
Gigster launched as a simple landing page with chat
“So Gigster itself was basically a landing page that said, hire a quality developer in five minutes. And then it had a simple chat application on the backend that you could use to chat with us and hire said developer.”
Gigster received $3M in project submissions within 24 hours of launch
“So we launched Gigster November, December, twenty-fourteen, pretty much the same week that we launched. Actually, it was, I believe, within one or two days, we had three million dollars worth of business submitted. Literally, I think it was the first 24 hours.”
Gigster's average project size grew from $20k to $150k between rounds
“Between our series A and our series B, which is roughly 20 15 to 20 16, we saw our average project size go up from 15 or 20,000 to about a 150,000.”
Andreessen Horowitz employs 150 operating partners, according to Roger Dickey
“I think they have a 150 operating partners at the firm.”
Roger Dickey claims Andreessen Horowitz adds as much value as a co-founder
“And I think, you know, one of the ways we think about it is in Andreessen Owen's Some large percentage of our company, let's say, 10 to 20% of the company, we think of them like a co-founder, and they actually have added the same level of value that a co-found…”
Andreessen Horowitz spent 15 minutes on founder backgrounds before Gigster's pitch
“When we went to the partner meeting, the final approval meeting for our investment with Andreessen, I think they asked us to talk about ourselves for about 10 or 15 minutes before the pitch”
Roger Dickey prioritizes target market over team or product in angel investing
“Of all those things, market is the first thing I look at when I'm making an angel investment because I've actually seen, I've now been investing long enough that I've seen great founders pursue terrible markets and the businesses just don't go anywhere.”
Roger Dickey: Engineering job openings outnumber existing software engineers five to one
“There's a five to one ratio of job openings for engineers to engineers that actually exist.”
Roger Dickey warns most people shouldn't angel invest expecting financial returns
“It's the kind of thing most people shouldn't really be doing expecting a financial return.”
Roger Dickey admits over 50 of his angel investments haven't returned capital
“So in, in, in my case, I have 40 or 50 companies that probably, probably 50 plus companies that haven't returned yet.”
Roger Dickey compares LPing in Sequoia or Andreessen to a mutual fund
“Like if you can LP with Sequoia Greylock, Kleiner, Andreessen, you're probably going to get your money back. You know, that's almost like a mutual fund.”
Roger Dickey predicts a higher-level language will soon simplify software creation
“I believe that there will be a higher level language for software that makes software Easier to build. You know, we've gone from assembly to, you know, C++ to JavaScript, now to these web frameworks. I think there's going to be something even higher level than…”
Roger Dickey claimed in 2017 that social app venture opportunities were dead
“I don't think there are opportunities in, in social or photo sharing apps right now.”
Roger Dickey predicted in 2017 that most seed-stage AI investments would fail
“I think artificial intelligence is the wave. It's that's the trend right now that's forming new companies. So you have a lot of people that are investing in teams that probably aren't the best teams to be going after those opportunities. I think there are goin…”