Apr 14, 2017 · 30m · 20vc
20VC: How Investors Can Get Into The Best Deals & Why Founders First Point Of Contact Should Be With The Investment Decision-Maker with Spencer Kimball, Founder & CEO @ Cockroach Labs
0:00 / 0:00
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, Spencer Kimball, Founder and CEO of Cockroach Labs, joins Harry Stebbings to discuss database innovation, effective strategies for VCs to win competitive deals, and lessons on company culture and founder-investor relationships.
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 25.7% of the talking time here. How this is scored →
Harry as informed peer 2.2 Guest teaching 4.7 Guest disagreement 2.0 Harry pushing back 1.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 11:22 Spencer dismisses VC associates as flunkies
Spencer aggressively criticizes VCs who send junior associates to initial founder meetings, describing the experience as a major turnoff and referring to junior staff as flunkies.
Hardest push from Harry ▶ 13:13 Harry presses Spencer on avoiding associate meetingsHarry refuses Spencer's blanket dismissal of junior VC staff, directly asking whether founders should simply refrain from wasting time with non-investing partners.
Biggest teaching moment ▶ 11:22 Spencer breaks down ideal VC operational structuresSpencer educates the host on why Benchmark's lean partner-direct model outperforms larger funds that place associate gatekeepers between decision-makers and founders.
Harry holds his own ▶ 13:13 Harry challenges Spencer's rigid stance on associatesHarry pushes Spencer into conceding that associates can actually provide valuable feedback, leading Spencer to share an anecdote about hiring a VC associate as a product manager.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Podcast Audio Interlude | 1 | 5 | 0 | 0 | Harry introduces the episode and asks a standard background question regarding Spencer's aha moment for Cockroach Labs. Spencer provides an extended history of database scaling challenges at Google and Square, educating the audience on technologies like BigTable and Spanner. | |
| The Strategic Value of Founder-VC Conversations | 2 | 4 | 1 | 1 | Harry asks Spencer why he uniquely enjoys meeting with every VC. Spencer explains his reasoning, reframing VC interactions as valuable external stress-tests for company vision. | |
| Constructive Feedback and Radical Candor from Investors | 3 | 4 | 3 | 2 | Harry asks how investors should deliver feedback and what signals indicate a poor relationship. Spencer criticizes lowballing and overly adversarial term sheet negotiations, comparing bad VCs to used car salesmen. | |
| How Decision-Makers Win Competitive Investment Deals | 3 | 6 | 5 | 2 | Harry asks how VCs can win competitive deals. Spencer strongly criticizes firms that deploy junior associates as initial contacts, referring to them as flunkies and praising Benchmark's direct-partner model. | |
| Evaluating Partner Involvement Versus Support Staff | 4 | 5 | 3 | 4 | Harry challenges Spencer's stance by asking if founders should avoid non-investing partners entirely. Spencer reframes the point, noting he actually poached an associate as a PM, while maintaining that partner involvement is vital for real execution. | |
| Winning Secondary Funding Allocations Through Relationship Building | 2 | 4 | 2 | 1 | Harry prompts Spencer on how VCs can win secondary funding rounds. Spencer notes that most VCs promise to stay in touch but disappear until news leaks, advising VCs to maintain proactive relationship building. | |
| Company Culture and Free Fridays at Cockroach Labs | 2 | 5 | 2 | 1 | Harry inquires about Cockroach's reported four-day workweek. Spencer corrects the premise, explaining that they practice Free Fridays and breaking down why Google's 20 percent time policy failed. | |
| Quick Fire Q&A Round with Spencer Kimball | 2 | 5 | 2 | 2 | Harry runs a quick-fire round where Spencer ignores time limits to give detailed answers on Roman history and macroeconomic theory. Harry teasingly calls out the long answer format. | |
| The Five-Year Product Vision for Cockroach Labs | 1 | 4 | 0 | 0 | Harry asks about the five-year vision for Cockroach Labs. Spencer explains multi-region cloud databases, latency challenges, and global data sovereignty compliance. |
Statements from this episode (16)
Kimball: Google's Bigtable spawned the entire NoSQL movement
“They built first big table, which really spawned the entire NoSQL movement that's with us today.”
Kimball: Google replaced all sharded MySQL with Spanner and Bigtable
“Spanner is the database technology that Google has used to consolidate all of their various applications on top of. So they no longer use Sharded MySQL. Everything's on Spanner or on Bigtable.”
Kimball: Proactive VCs with clear theses are the most helpful
“I actually happen to find the venture capitalists that find me to be the most helpful because they already have a thesis that they're working from.”
Kimball: Pitching new VCs provides valuable test-audience feedback
“It's kind of like a test audience where you can give the pitch, you can talk about the vision, and you can either have crickets on the other end, or you can have someone that's very enthusiastic, and that's often a very good signal I've found.”
Kimball: Lowball VC negotiation tactics damage founder trust and board relationships
“So, you know, like you establish that trust early and I'm sorry, but like the, a very chaotic and unpleasant negotiation phase is not a good way to, you know, have then, you know, have that person transition onto your board. I know I think that there's a much …”
Kimball: VCs win competitive deals when decision-makers lead founder outreach
“For the initial deal, the best way to get in is to have the true decision maker be the main point of contact for the company.”
Kimball: Benchmark operates with equal partner ownership and no support staff
“There's no more opposite approach in the industry than the one that Benchmark takes, for example. And this is a very small VC fund, you know, not necessarily in dollars, although it's not, it's by far not the largest. But, you know, it's a small number of part…”
Kimball: Recruited VC associate as Cockroach Labs product manager
“There's somebody that I met with in exactly this capacity at one of the really big funds, and she was working in Palo Alto for them, and she was the one that I was interacting with, and I actually really liked her. I thought she was incredibly intelligent, rea…”
Kimball: GP advocacy is more valuable than VC platform support teams
“No matter how good the associate or the BV person or the BV team even, you know, in a much bigger VC, those guys are good, and they can do great work, and they can actually probably do more work in terms of volume, but I'd rather have Peter Fenton on the phone…”
Kimball: Top VCs Win Allocations by Staying Proactively Engaged Between Rounds
“But I think that what separates the wheat from the shaft there is that the really good VCs, the ones that really want to land the deal, assuming that is their priority, you know, these guys will, and gals, will stay in touch, and they'll be proactive about it.”
Kimball: Cockroach Labs Rejects Late-Arriving VCs Who Skipped Between-Round Touchpoints
“And then many of the VCs that I talked to in the previous round, they start to hear about it through the grapevine, and then they pop up, and they want to be involved, and no matter how much I like them, it's often pretty far along at that point, usually past …”
Spencer Kimball: Google's 20% time was a failed policy
“What happened at Google was that nobody really took the 20% time. It was a little bit of a failed policy.”
Kimball: Dedicated Free Fridays yield higher worker satisfaction than traditional weeks
“I think that ultimately leads to a much happier work environment in the sense that you're able to balance the sort of grind of those four days, which honestly people put a little bit more effort into those four days, but then you still have that fifth day wher…”
Kimball: Ben Bernanke and Paul Krugman's macroeconomic forecasts blow everyone else away
“I'd say that their track record in terms of, you know, prognostications is incredibly good. I mean, it just blows everyone else out of the water.”