Oct 21, 2016 · 30m · 20vc
20VC: Why Adaptability Is Key To Fundraising, Why Supply Is Always The First Priority In Marketplaces & Why Sometimes You Have To Hire Fast & Fire Fast with Nav Athwal, Founder & CEO @ RealtyShares
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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 Nav Athwal, Founder and CEO of RealtyShares, to discuss real estate marketplaces, startup scaling, fundraising across changing market cycles, and valuation realism. Athwal shares actionable insights on marketplace supply dynamics, organizational hiring, regulatory compliance, and aligning with strategic board partners.
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 27.3% of the talking time here. How this is scored →
Harry as informed peer 2.5 Guest teaching 2.5 Guest disagreement 0.5 Harry pushing back 0.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:03 Contrarian view on hiring speed
Nav politely pushes back against the widely accepted startup wisdom of 'hire slow, fire fast', asserting that founders must move quickly when exceptional talent is available to avoid analysis paralysis.
Hardest push from Harry ▶ 6:59 Challenging the generalizability of supply-side focusHarry pushes Nav on whether focusing on supply first is a universal rule for all vertical marketplaces or simply a quirk of real estate.
Biggest teaching moment ▶ 7:11 Explaining friction in marketplace supply vs demand dynamicsNav educates Harry on why supply side partners have more patience than end consumers, drawing concrete examples from Uber and Airbnb to demonstrate how supply deficits kill demand.
Harry holds his own ▶ 21:53 Pressing on valuation traps and Series B readinessHarry shows sophisticated understanding of venture capital cycles by asking whether founders should artificially temper valuations in Series A rounds to avoid failing at Series B.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Founding RealtyShares and the Disparity in Real Estate Capital | 3 | 3 | 1 | 1 | Harry demonstrates interest in marketplace mechanics, asking specific questions about supply versus demand dynamics and macroeconomic sensitivity. Nav elaborates on real estate capital disparities and why supply must be solved before demand to prevent user friction. | |
| Scaling Company Infrastructure, Culture, and Compliance | 2 | 2 | 0 | 0 | Harry asks about internal organizational shifts during rapid scaling. Nav outlines two core pillars: internal communication/culture and operating within strict SEC compliance under the motto 'move fast without breaking things'. | |
| Employee Adaptation and Growth Across Startup Stages | 2 | 2 | 0 | 1 | Harry probes whether early employees can scale with a startup through to late stages or if employee churn is inevitable. Nav provides a balanced perspective, explaining his CEO ethos of giving everyone the chance to scale while recognizing that role specialization naturally causes churn. | |
| Hiring Philosophy: Balancing IQ, EQ, and Execution Speed | 2 | 3 | 2 | 0 | Harry asks about hiring philosophies beyond IQ. Nav gently offers a contrarian perspective on the classic phrase 'hire slow and fire fast,' arguing that execution speed requires founders to hire fast when top talent is present. | |
| Fundraising Experiences Across Seed, Series A, and Series B | 3 | 3 | 0 | 0 | Harry references top VC backers like General Catalyst, Menlo, and USV, prompting Nav to break down his fundraising experiences. Nav details how the Series A was easy in a booming market, whereas the Series B required extreme adaptability as VC sentiment cooled. | |
| Valuation Realism and Prioritizing Board Partnership | 3 | 2 | 0 | 1 | Harry questions whether founders should maintain valuation realism in boom times to protect future rounds. Nav agrees, explaining that optimizing for board alignment over peak valuation prevents the deadly trap of unachievable growth expectations. |
Statements from this episode (16)
RealtyShares surpasses $200 million in funded deals with top VC backing
“RealtyShares recently announced an incredible two hundred million funded deals through the platform, so a huge congratulations to them. For that, and they've also raised funding from some of the world's best investors, including the one and only Union Square V…”
RealtyShares real estate investments yielded 8% to 9% or more in 2013
“Back in 2013 when, you know, this exists today where yields were really, really low. So we also benefited from a very low yield environment where a lot of our investments were paying eight, nine percent or more And you were getting half a percent in your bank …”
Marketplace startups must solve supply before demand to ensure good user experiences
“You know, I think supply is the area to focus on first, because if you don't have a product for the demand side, that experience Your experience is going to be pretty bad, and your earliest buyers are probably going to be your biggest proponents, and then the …”
Regulated startups must move fast without breaking things to avoid regulatory ruin
“The motto we mentioned here is sort of a play on, on the Facebook motto of move fast and break things. Our motto is move fast without breaking things because, you know, you can't afford to break things when you're regulated.”
US financial regulations date back to the 1930s and 1940s
“A lot of these laws were passed in the, you know, the thirties and forties when the internet didn't exist.”
Any startup employee can grow with the company as it scales
“I think as a CEO of realty shares, the kind of position I always take is any employee can grow with the company and it's their sort of job to lose.”
Incubator networks remain valuable to founders through the Series B stage
“So that network really is strong and it's, you know, not only been a value when we were a seed stage company, but has continued to prove valuable as we've shifted to a series B company.”
Founders should hire fast to avoid missing out on strong candidates
“There's a saying that says hire slow and fire fast. You know, I think there's components of that that are true, but really I think there's a lot of times where you should hire fast and not, not hire slow. And I think you know, I think ultimately when you have,…”
Technology has barely changed the core real estate transaction process
“The real estate market again is a very massive market opportunity because there hasn't been a lot of efficiency created within the transactional process itself. There's obviously more access to information because of Zillow and Trulia, but the transaction proc…”
Series B rounds are difficult because venture capitalists pay premium valuations
“The Series B round naturally is a hard round, right, because, you know, VCs are not investing early where they're getting a great price. They're, you know, typically getting, paying up In a B and that company may or may not have hit an inflection point where t…”
Founders should begin fundraising well before reaching six months of runway
“Try to get in front of the fundraise. Don't raise when you are on, you know, on a six months of runway, try to raise earlier. Because ultimately you want enough flexibility where if you're not getting the right price for the round, you can go, you can afford t…”
High valuations during market booms create significant risks for follow-on fundraising rounds
“A lot of companies didn't raise that really high series A valuations or series B valuations because the market was very irrational. And now are having a hard time, you know, raising that next round, you know, because they weren't able to hit the growth metrics…”
Founders should optimize for investor alignment over slight valuation premiums
“Don't optimize for valuation, optimize for the company and the company that's investing in you and then the board member that's joining your company. And if there's a strong fit there, because ultimately there's not a big difference between what VCs and invest…”
RealtyShares gives every employee Ben Horowitz's 'Hard Thing About Hard Things'
“That has been a book that every employee at realty shares gets a copy of.”