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Apr 11, 2019 · 18m · top-founders

1356 Early Employee Who Wants to Sell A Few Shares? Plaza Ventures New Model Is What You Need.

Matthew Liebowitz · 9m spoken Nathan Latka · 7m spoken
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 interview, Nathan Latka speaks with Matthew Liebowitz, General Partner at Plaza Ventures, exploring how the Toronto-based firm pioneered Canada's first secondary tech fund and disrupted traditional venture capital with zero management fees, recurring fund structures, and targeted liquidity for early employees.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 43.1% of the talking time here. How this is scored →

Nathan as informed peer 5.0 Guest teaching 3.3 Guest disagreement 2.0 Nathan pushing back 4.0
05100:0010:000:00–4:33 · Nathan as informed peer 3/10 Book Promotion: How to Be a Capitalist Without Any Capital The segment begins with Nathan promoting his book and show intro before welcoming Matthew. Nathan asks baseline exploratory questions about Plaza Ventures' origin and fee structure, which Matthew answers cooperatively.4:33–6:34 · Nathan as informed peer 6/10 Differentiating the Fund Model and LP Transparency Nathan challenges the claimed differentiation of LP transparency by citing his own experience as an LP in traditional funds. Matthew counters by emphasizing their zero management fee structure and immediate capital deployment.6:35–10:24 · Nathan as informed peer 6/10 Creating Canada's First Secondary Market Fund Nathan invokes Social Capital's private liquidity strategy to probe whether the model is flawed, but Matthew clarifies that Plaza targets pre-IPO secondary employee buyouts rather than delaying IPOs.10:24–13:26 · Nathan as informed peer 7/10 Assisting Early Employees and Cleaning Cap Tables Nathan cites Infusionsoft's Goldman secondary round to question why founders wouldn't wait for large PE rounds. Matthew educates Nathan on off-balance sheet smaller checks and the unique scale of the Canadian tech ecosystem.13:26–16:25 · Nathan as informed peer 6/10 Acquiring Employee Options and Partnering with CEOs Nathan identifies the tactic of purchasing unexercised employee options, noting aggressive US practices. Matthew clarifies they operate strictly in partnership with the CEO rather than going around management.16:27–17:47 · Nathan as informed peer 2/10 The Famous Five Rapid-Fire Questions The conversation concludes with the standard rapid-fire questions covering software tools, sleep schedules, and personal reflection in a relaxed, friendly tone.0:00–4:33 · Guest teaching 2/10 Book Promotion: How to Be a Capitalist Without Any Capital The segment begins with Nathan promoting his book and show intro before welcoming Matthew. Nathan asks baseline exploratory questions about Plaza Ventures' origin and fee structure, which Matthew answers cooperatively.4:33–6:34 · Guest teaching 4/10 Differentiating the Fund Model and LP Transparency Nathan challenges the claimed differentiation of LP transparency by citing his own experience as an LP in traditional funds. Matthew counters by emphasizing their zero management fee structure and immediate capital deployment.6:35–10:24 · Guest teaching 5/10 Creating Canada's First Secondary Market Fund Nathan invokes Social Capital's private liquidity strategy to probe whether the model is flawed, but Matthew clarifies that Plaza targets pre-IPO secondary employee buyouts rather than delaying IPOs.10:24–13:26 · Guest teaching 5/10 Assisting Early Employees and Cleaning Cap Tables Nathan cites Infusionsoft's Goldman secondary round to question why founders wouldn't wait for large PE rounds. Matthew educates Nathan on off-balance sheet smaller checks and the unique scale of the Canadian tech ecosystem.13:26–16:25 · Guest teaching 3/10 Acquiring Employee Options and Partnering with CEOs Nathan identifies the tactic of purchasing unexercised employee options, noting aggressive US practices. Matthew clarifies they operate strictly in partnership with the CEO rather than going around management.16:27–17:47 · Guest teaching 1/10 The Famous Five Rapid-Fire Questions The conversation concludes with the standard rapid-fire questions covering software tools, sleep schedules, and personal reflection in a relaxed, friendly tone.0:00–4:33 · Guest disagreement 1/10 Book Promotion: How to Be a Capitalist Without Any Capital The segment begins with Nathan promoting his book and show intro before welcoming Matthew. Nathan asks baseline exploratory questions about Plaza Ventures' origin and fee structure, which Matthew answers cooperatively.4:33–6:34 · Guest disagreement 2/10 Differentiating the Fund Model and LP Transparency Nathan challenges the claimed differentiation of LP transparency by citing his own experience as an LP in traditional funds. Matthew counters by emphasizing their zero management fee structure and immediate capital deployment.6:35–10:24 · Guest disagreement 3/10 Creating Canada's First Secondary Market Fund Nathan invokes Social Capital's private liquidity strategy to probe whether the model is flawed, but Matthew clarifies that Plaza targets pre-IPO secondary employee buyouts rather than delaying IPOs.10:24–13:26 · Guest disagreement 2/10 Assisting Early Employees and Cleaning Cap Tables Nathan cites Infusionsoft's Goldman secondary round to question why founders wouldn't wait for large PE rounds. Matthew educates Nathan on off-balance sheet smaller checks and the unique scale of the Canadian tech ecosystem.13:26–16:25 · Guest disagreement 3/10 Acquiring Employee Options and Partnering with CEOs Nathan identifies the tactic of purchasing unexercised employee options, noting aggressive US practices. Matthew clarifies they operate strictly in partnership with the CEO rather than going around management.16:27–17:47 · Guest disagreement 1/10 The Famous Five Rapid-Fire Questions The conversation concludes with the standard rapid-fire questions covering software tools, sleep schedules, and personal reflection in a relaxed, friendly tone.0:00–4:33 · Nathan pushing back 2/10 Book Promotion: How to Be a Capitalist Without Any Capital The segment begins with Nathan promoting his book and show intro before welcoming Matthew. Nathan asks baseline exploratory questions about Plaza Ventures' origin and fee structure, which Matthew answers cooperatively.4:33–6:34 · Nathan pushing back 6/10 Differentiating the Fund Model and LP Transparency Nathan challenges the claimed differentiation of LP transparency by citing his own experience as an LP in traditional funds. Matthew counters by emphasizing their zero management fee structure and immediate capital deployment.6:35–10:24 · Nathan pushing back 5/10 Creating Canada's First Secondary Market Fund Nathan invokes Social Capital's private liquidity strategy to probe whether the model is flawed, but Matthew clarifies that Plaza targets pre-IPO secondary employee buyouts rather than delaying IPOs.10:24–13:26 · Nathan pushing back 6/10 Assisting Early Employees and Cleaning Cap Tables Nathan cites Infusionsoft's Goldman secondary round to question why founders wouldn't wait for large PE rounds. Matthew educates Nathan on off-balance sheet smaller checks and the unique scale of the Canadian tech ecosystem.13:26–16:25 · Nathan pushing back 4/10 Acquiring Employee Options and Partnering with CEOs Nathan identifies the tactic of purchasing unexercised employee options, noting aggressive US practices. Matthew clarifies they operate strictly in partnership with the CEO rather than going around management.16:27–17:47 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions The conversation concludes with the standard rapid-fire questions covering software tools, sleep schedules, and personal reflection in a relaxed, friendly tone.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 79.3% · guest 20.7%0:00 · Nathan 79.3% · guest 20.7%3:00 · Nathan 30.9% · guest 69.1%3:00 · Nathan 30.9% · guest 69.1%6:00 · Nathan 33% · guest 67%6:00 · Nathan 33% · guest 67%9:00 · Nathan 17.6% · guest 82.4%9:00 · Nathan 17.6% · guest 82.4%12:00 · Nathan 48.8% · guest 51.2%12:00 · Nathan 48.8% · guest 51.2%15:00 · Nathan 42.4% · guest 57.6%15:00 · Nathan 42.4% · guest 57.6%18:00 · Nathan 94.9% · guest 5.1%18:00 · Nathan 94.9% · guest 5.1%
Sharpest disagreement ▶ 16:06 Deflecting specific exit return questions

Matthew refuses to name which portfolio exit was most profitable, asserting NDA constraints and using humor to avoid Nathan's direct probing.

 Hardest push from Nathan ▶ 5:43 Pushback on LP fund transparency

Nathan directly challenges Matthew's value proposition by stating that regular VC funds already provide detailed monthly updates to LPs.

 Biggest teaching moment ▶ 10:49 Explaining off-balance sheet cap table cleanups

Matthew explains the structural difference between $40M–$200M institutional PE checks and Plaza's smaller $3M–$5M off-balance sheet secondaries designed to reward early garage-era employees.

 Nathan holds their own ▶ 12:04 Nathan cites Infusionsoft Goldman liquidity case

Nathan demonstrates industry expertise by referencing his detailed interview with Infusionsoft's CEO regarding employee liquidity tranches during their Goldman Sachs round.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Book Promotion: How to Be a Capitalist Without Any Capital 3212 The segment begins with Nathan promoting his book and show intro before welcoming Matthew. Nathan asks baseline exploratory questions about Plaza Ventures' origin and fee structure, which Matthew answers cooperatively.
Differentiating the Fund Model and LP Transparency 6426 Nathan challenges the claimed differentiation of LP transparency by citing his own experience as an LP in traditional funds. Matthew counters by emphasizing their zero management fee structure and immediate capital deployment.
Creating Canada's First Secondary Market Fund 6535 Nathan invokes Social Capital's private liquidity strategy to probe whether the model is flawed, but Matthew clarifies that Plaza targets pre-IPO secondary employee buyouts rather than delaying IPOs.
Assisting Early Employees and Cleaning Cap Tables 7526 Nathan cites Infusionsoft's Goldman secondary round to question why founders wouldn't wait for large PE rounds. Matthew educates Nathan on off-balance sheet smaller checks and the unique scale of the Canadian tech ecosystem.
Acquiring Employee Options and Partnering with CEOs 6334 Nathan identifies the tactic of purchasing unexercised employee options, noting aggressive US practices. Matthew clarifies they operate strictly in partnership with the CEO rather than going around management.
The Famous Five Rapid-Fire Questions 2111 The conversation concludes with the standard rapid-fire questions covering software tools, sleep schedules, and personal reflection in a relaxed, friendly tone.

Statements from this episode (11)

Disclosure
Plaza Ventures raises annual funds, seeding one-third with internal capital
“So instead of raising a large one year, 10 year monolithic fund, we raise one or two funds every year. We seed each of the fund with about a third of our own capital.”
Matthew Liebowitz Apr 11, 2019 ▶ 2:58
Disclosure
Plaza Ventures operates on a zero-fee, 20 percent carry model
“We don't actually charge any management fees in any of our funds. We take a 20% carried interest after a hundred percent return to capital. So, so think of us as a zero and 20 model.”
Matthew Liebowitz Apr 11, 2019 ▶ 3:36
Disclosure
Plaza Ventures Deploys 40% to 60% of Capital on Day One
“Whereas what we're saying to our LPs is, Hey, here's where typically 40 to 60% of your capital is going on day one. So we've already diligenced these companies, and we basically raise a fund in lockstep with doing the investments.”
Matthew Liebowitz Apr 11, 2019 ▶ 5:05
Disclosure
Plaza Ventures targets secondary shares from angel investors and early employees
“So we're actually buying shares primarily from either early angel investors and or early ex-employees in late-stage private, pre-IPO, pre-M&A, pre-private equity investment and or change of control transaction companies.”
Matthew Liebowitz Apr 11, 2019 ▶ 6:59
Assertion Supported
Plaza Ventures is the first dedicated tech secondary fund in Canada
“There's definitely, we identified about 40 groups in the U.S. That do this either as a core focus and or a sleeve on their platform, but we're first to market, believe it or not, in Canada.”
Matthew Liebowitz Apr 11, 2019 ▶ 7:14
Assertion Not checkable as stated
Canadian tech companies now scale to $100M+ revenue before exiting
“It used to be that you know, a company would get to five, ten million revenue and then sell. Now companies are much more bullish and are looking to go to a hundred million plus in revenue, and thus they have a lot more of an employee base that's underneath the…”
Matthew Liebowitz Apr 11, 2019 ▶ 7:54
Disclosure
Plaza Ventures Targets 18 to 36 Month Secondary Liquidity Windows
“So we are not buying out other VC funds. We're not, the pitch is to the, to management is not, Hey, We're investing in your company and thus it could delay an IPO. It's actually quite the opposite. We're actually going down a level or two and going and buying …”
Matthew Liebowitz Apr 11, 2019 ▶ 8:56
Disclosure
Plaza Ventures typically writes $3M to $5M secondary checks
“So we're doing typically off-balance sheet investments, so these are secondaries. It doesn't hit their It, the board typically doesn't have to convene on these deals. They're much smaller in nature. They're typically three or four or five million dollars in n…”
Matthew Liebowitz Apr 11, 2019 ▶ 10:49
Assertion Not checkable as stated
Plaza Ventures executes employee secondaries in lockstep with company CEOs
“So we're not going around the CEO. We're doing it in lockstep with them in parallel with them. And in fact, in every deal we've done thus far in every transaction we're looking at thus far, frankly, the CEO is our number one champion. And they've actually been…”
Matthew Liebowitz Apr 11, 2019 ▶ 14:12
Opinion
A Bloomberg Terminal for private tech shares is a massive market opportunity
“There's no dare I say, Bloomberg terminal private shares of later stage private tech companies. I'd love, I wish there was, that would certainly perhaps make my life a little bit easier. But having said that I think that would be a great opportunity.”
Matthew Liebowitz Apr 11, 2019 ▶ 14:43
Disclosure
Plaza Ventures closed a $50 million secondary fund
“It's a fifty million dollar fund.”
Matthew Liebowitz Apr 11, 2019 ▶ 15:10
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