Feb 18, 2021 · 44m · 20vc
20VC Special: The Real Estate Fintech OGs on Why This Is Not The End For The Bay Area and What Can Be Done To Solve It, The Pros and Cons of Working with Corporate Investors and How Leading Their Teams Has Fundamentally Changed in a COVID World
Brendan Wallace · 10m spoken Harry Stebbings · 9m spoken Max Simkoff · 8m spoken Nima Gamsari · 7m spoken Assaf Wand · 6m spoken
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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 milestone episode of TwentyVC, host Harry Stebbings brings together proptech and real estate fintech leaders Asaf Wand, Nima Gamsari, Max Simkoff, and Brendan Wallace to discuss company building, Silicon Valley's future, corporate venture capital, and leadership through disruption.
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 21.7% of the talking time here. How this is scored →
Harry as informed peer 2.4 Guest teaching 2.7 Guest disagreement 2.0 Harry pushing back 1.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:35 Brandon challenges Max's Silicon Valley defense
Brandon directly counters Max's defense of the Bay Area, arguing that Silicon Valley's echo chamber leads VCs to fund trivial ideas like Juicero while missing massive industries like proptech.
Hardest push from Harry ▶ 16:28 Harry queries tax and liquidity drivers of exodusHarry interrupts the philosophical discussion on Bay Area culture to challenge the guests on whether the exodus is primarily driven by tax optimization following major IPO liquidity events.
Biggest teaching moment ▶ 32:41 Brandon reveals the reality of corporate VC inertiaBrandon reframes the discussion around corporate partnerships by exposing that corporate incumbents initially rejected now-billion-dollar proptech models like States Title and Hippo.
Harry holds his own ▶ 25:14 Harry probes structural fund implicationsHarry demonstrates domain insight by questioning how corporate tech adoption forces VCs to build hyper-verticalized offerings or raise mega-funds to capitalize on capital flows.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Panelist Introductions and Company Missions | 2 | 1 | 1 | 1 | Harry sets up the episode with light moderating and warm banter, allowing the founders and VC to exchange mutual accolades. The panel dynamic is highly collaborative as guests outline their respect and learnings from each other. | |
| Debates on Enterprise Strategy vs. Direct-to-Consumer | 2 | 3 | 3 | 1 | Harry prompts Nima to share historical debates regarding enterprise software versus direct-to-consumer strategies. Brandon offers a mild rebuttal regarding the lack of innovation within venture capital itself, slightly challenging Nima's framing. | |
| The Bay Area Exodus and Future of Silicon Valley | 3 | 4 | 4 | 2 | Harry introduces the controversial Bay Area exodus topic and later pushes on whether tax incentives drive the movement. Max forcefully criticizes outbound founders who trash the region, while Brandon counters that Silicon Valley suffers from a narrow echo chamber that overlooked major sectors like proptech. | |
| Evolution of Leadership During the Pandemic | 1 | 2 | 1 | 1 | Harry poses broad questions about management changes during the pandemic. Asaf and Max provide introspective answers about transparent communication and the challenges of remote culture without any host friction. | |
| Strategic Shift in Corporate Real Estate and PropTech Adoption | 4 | 3 | 1 | 2 | Harry asks a targeted follow-up on how corporate tech adoption alters Fifth Wall's fund strategy. Brandon outlines the expanding $64 billion proptech landscape and its distinct subsectors. | |
| The Reality of Corporate VCs and Fundraising Truths | 2 | 4 | 3 | 1 | Harry asks about ideal investor qualities across growth stages. Brandon reframes the panel's praise of corporate VCs by sharing the dark reality that traditional corporates initially rejected now-massive companies like States Title and Hippo. | |
| Quick-Fire Round with Panelists | 3 | 2 | 1 | 1 | Harry leads a rapid-fire round touching on personal traits, books, and board dynamics. Brandon playful teases Harry for asking a generic LP question about five-year market predictions. |
Statements from this episode (24)
Stebbings: Proptech leaders will build hundreds of billions in enterprise value
“These founders are all absolute OGs of the financial real estate market, building companies that I believe will represent hundreds of billions of dollars in enterprise value over the coming years”
Gamsari: Blend powers 30% to 40% of all US mortgage lenders
“We work with about 30 to 40% of lenders in the country to power their mortgage process in particular.”
Simkoff: States Title became the eighth-largest US title business in five years
“We're only four or five years old now, but have already become the eighth largest title in closing business in the United States, and well on our way to becoming number one.”
Simkoff: Naivete is a founder's most dangerously powerful skill
“The more you know about an industry, the more reasons you have not to start a company or grow a business, right? It's too hard. Did you like understand the competitive landscape? I don't know if you remember this conversation, but we talked about how like naiv…”
Simkoff: VCs resist specialization because they hate extinguishing option value
“The one thing VCs hate is extinguishing option value. So, like, when you're in a meeting with them, you're like, what's your typical investment size? Well, we do Series B and C. You're like, oh, we're looking for And they're like, oh, we do seed investments to…”
Wallace: Fifth Wall invested in Hippo before finishing its first fund
“We hadn't even raised our fund. And the soft was like, you need to invest in our business. And I was like, I don't even have a fund yet. I don't know how I'm possibly going to do that. But ultimately we did.”
Wallace: States Title bought an entire business unit from a corporate LP
“Our idea was our corporates would just buy the products of the tech companies we were investing in. We didn't contemplate that our startups would be buying entire businesses from our corporates, which is precisely what Max did.”
Wallace: Venture capital is a boring industry that has never been disrupted
“VC is a pretty boring industry. Talk about an industry that's never been disrupted, right?”
Simkoff: The Bay Area will grow stronger despite recent tech exodus
“This area is going to only get stronger as a result of the dynamic change that's going through.”
Wallace: Silicon Valley echo chamber caused VCs to overlook proptech
“I do think there's an echo chamber that exists in Silicon Valley that has actually perpetuated some of the problems in venture capital in the Bay Area and overlooking huge categories like prop tech.”
Wand: Silicon Valley remains the best place to scale a company
“If you want to build a company to scale, it's probably the best place in the world to build it, and it's because of the people that you have around.”
Gamsari: Blend pays new college graduates $150K to $160K starting salaries
“The new grads that we hire at blend, we pay them, you know, a 150, a 160 K.”
Gamsari: San Francisco will take a massive long-term economic hit
“I do think San Francisco is going to take a really big hit. San Francisco in particular, maybe California more broadly, but San Francisco in particular is going to take a huge hit.”
Wand: Remote work creates a mercenary culture and increases employee turnover
“This remote work environment creates a bit of a mercenary environment because you never built any relationship with the a person. You never infused the culture of the company. So it's not a really big problem for them to leave and to move.”
Asaf Wand: Remote Work Inhibits Creativity and Complex Problem-Solving
“I think it's very, very difficult to do creative things and solve hard problems. The actual amount of work that's done on some silos is probably fine for engineers. They still close more tickets. Potentially they don't have commute. Maybe it's effective, but t…”
Max Simkoff: Admitting Uncertainty to Staff is Comforting During Crises
“In times of crisis, people like to assume that leaders Have a very specific strategy and they've mapped everything out and they know what to do. And the reality is like, we're just winging it. And sometimes when you tell people that that's what you're doing, t…”
Wallace: $64 billion was invested in proptech from 2016 to 2021
“Now, sixty four billion dollars has gone into the category in just the last five years.”
Simkoff: Lennar became States Title's largest shareholder after selling them a business
“Our largest single shareholder, still a minority shareholder, but the largest shareholder on our cap table is Lenar, who Fifth Wall introduced us to, and they became our largest shareholder because we bought their legacy title business, which gave us a ton of …”
Wand: Scaling $10M to $100M ARR is much harder than $1M to $10M
“It's a lot harder to go from ten million dollars to a hundred million dollars than a million dollars to ten million dollars, and it's not an easy route, and a lot of people fall along the way, and I think that's one of the things that nobody talks about.”
Wallace: Left to their own devices, corporate VCs make terrible decisions
“While they have all this potential left to their own devices, corporates will make terrible decisions.”
Wallace: Fifth Wall manages $1.4B and counts 4 top US homebuilders as LPs
“We're now with a 1,000,000,004 under management. We have four of the top five home builders as strategic LPs in our fund.”
Wallace: Corporate investors now account for 45% of all venture capital dollars
“Corporate investors represent 45% of all dollars into venture capital.”