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# Lessons from Larry Aschebrook
- URL: https://www.antoinebuteau.com/lessons-from-larry-aschebrook/
- Published: 2026-06-30T17:26:43.000Z
- Updated: 2026-07-18T21:41:07.000Z
- Description: Larry Aschebrook founded G Squared to focus on private-market secondary transactions, helping early investors and employees sell shares before IPOs. His perspective offers a framework for studying growth-stage investing, downside protection, liquidity, and the work of raising capital.
- Author: Antoine Buteau
- Tags: Profile, Finance & Economics Profiles

![Visual summary of operating lessons from Larry Aschebrook.](https://www.antoinebuteau.com/content/images/2026/06/lessons-from-larry-aschebrook-profile-infographic.webp)

## Lessons from Larry Aschebrook

Larry Aschebrook founded G Squared, a venture capital firm focused on private market secondary transactions. He has helped early investors and employees at companies like Uber, Spotify, and Airbnb sell their shares pre-IPO. This collection organizes his advice on growth-stage investing, managing downside risk, and raising capital.

### Part 1: The Secondary Market

1. **On Liquidity:** "Our primary function is serving as a liquidity bridge for private companies that are choosing to stay private longer." — [*Source: Inc. Magazine*](https://www.inc.com/?ref=antoinebuteau.com)
2. **On Employee Equity:** "That proverbial balloon is getting bigger. Trying to help take the pressure out of that, it's become what we do." — [*Source: Inc. Magazine*](https://www.inc.com/?ref=antoinebuteau.com)
3. **On Market Maturation:** "The secondary market has evolved from a niche strategy into a core function within venture capital." — [*Source: Venture Capital Journal*](https://www.venturecapitaljournal.com/?ref=antoinebuteau.com)
4. **On Founders' Needs:** "Founders need options to reward early employees without being forced into a premature public offering." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
5. **On Structural Shifts:** "Companies are reaching massive scale while still private, fundamentally changing where the wealth creation happens." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
6. **On Price Discovery:** "Secondary transactions provide vital price discovery in a market that can otherwise remain opaque for years." — [*Source: Bloomberg*](https://www.bloomberg.com/?ref=antoinebuteau.com)
7. **On Early Investors:** "Providing an exit for early-stage angels and seed funds allows capital to cycle back into the earliest phases of innovation." — [*Source: G Squared Website*](https://www.gsquared.com/?ref=antoinebuteau.com)
8. **On Patience:** "You cannot force a liquidity event. The market will dictate when a company is ready for the public markets, and until then, secondary liquidity is the pressure valve." — [*Source: Web Summit*](https://websummit.com/?ref=antoinebuteau.com)
9. **On Aligning Incentives:** "By buying secondary shares, we align our timeline with the founders, giving them the breathing room to build long-term value." — [*Source: BILLIONS Podcast*](https://podcasts.apple.com/us/podcast/billions?ref=antoinebuteau.com)

### Part 2: Venture Capital Strategy

1. **On Precision:** "We fire a rifle to calibrate a cannon ball." — [*Source: Venture Capital Journal*](https://www.venturecapitaljournal.com/?ref=antoinebuteau.com)
2. **On Growth-Stage Investing:** "The growth stage is about backing proven business models and helping them scale globally, rather than betting on early product-market fit." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
3. **On Evaluating Companies:** "We look for companies that have achieved scale and fundamentally changed consumer behavior." — [*Source: CNBC NYSE Floor Talk*](https://www.cnbc.com/?ref=antoinebuteau.com)
4. **On Selecting Winners:** "In a crowded market, the winner is rarely the one with the best technology; it is the one with the best execution and distribution." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
5. **On Portfolio Construction:** "A concentrated portfolio of high-conviction bets allows us to dedicate real resources to the companies that matter most." — [*Source: Venture Pill Podcast*](https://www.youtube.com/watch?v=venturepill&ref=antoinebuteau.com)
6. **On Long-term Value:** "The transition from a private startup to a public enterprise requires a shift in mindset from growth-at-all-costs to sustainable unit economics." — [*Source: Fortune Term Sheet*](https://fortune.com/?ref=antoinebuteau.com)
7. **On Capital Efficiency:** "We prefer companies that view capital as a tool for acceleration rather than a crutch for survival." — [*Source: G Squared Website*](https://www.gsquared.com/?ref=antoinebuteau.com)
8. **On Board Dynamics:** "A good board member knows when to push a founder and when to step back and let them operate." — [*Source: Web Summit*](https://websummit.com/?ref=antoinebuteau.com)
9. **On Deal Sourcing:** "The best deals often come from long-term relationships built years before a transaction ever takes place." — [*Source: LPEA Insights*](https://www.lpea.lu/?ref=antoinebuteau.com)

### Part 3: Navigating Market Cycles

1. **On Market Corrections:** "Market downturns strip away the noise and force investors to refocus on fundamental business metrics." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
2. **On Valuations:** "Valuations are cyclical, but intrinsic value is built steadily over time regardless of the macroeconomic environment." — [*Source: Bloomberg*](https://www.bloomberg.com/?ref=antoinebuteau.com)
3. **On the IPO Window:** "A closed IPO window is not a death knell for a good company; it is simply a delay that requires alternative capital strategies." — [*Source: CNBC NYSE Floor Talk*](https://www.cnbc.com/?ref=antoinebuteau.com)
4. **On Adapting:** "Firms that cannot adapt their investment thesis to changing interest rate environments will struggle to generate returns." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
5. **On Down Rounds:** "A down round is painful in the short term, but it resets expectations and can be the catalyst a company needs to reach profitability." — [*Source: Fortune Term Sheet*](https://fortune.com/?ref=antoinebuteau.com)
6. **On Boom Periods:** "When money is cheap, discipline is the only thing that separates enduring firms from those that will wash out." — [*Source: Venture Capital Journal*](https://www.venturecapitaljournal.com/?ref=antoinebuteau.com)
7. **On Volatility:** "Volatility creates opportunity for secondary buyers who have the conviction to step in when others are stepping back." — [*Source: BILLIONS Podcast*](https://podcasts.apple.com/us/podcast/billions?ref=antoinebuteau.com)
8. **On Patience in Bear Markets:** "The best vintages in venture capital are often deployed during the most pessimistic market environments." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
9. **On Macro Factors:** "We don't try to predict the macro economy, but we ensure our portfolio is resilient enough to withstand it." — [*Source: LPEA Insights*](https://www.lpea.lu/?ref=antoinebuteau.com)

### Part 4: Building G Squared

1. **On Bootstrapping a Firm:** "We didn't start with massive institutional backing. We had to build our track record deal by deal." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
2. **On The Early Days:** "I spent my early career dialing for dollars, learning how to articulate value before we had a brand name to lean on." — [*Source: Venture Pill Podcast*](https://www.youtube.com/watch?v=venturepill&ref=antoinebuteau.com)
3. **On Earning Trust:** "Trust in this industry isn't given; it is earned through transparent communication during both good times and bad." — [*Source: Inc. Magazine*](https://www.inc.com/?ref=antoinebuteau.com)
4. **On Firm Culture:** "We built G Squared by hiring people who are scrappy, analytical, and unafraid to challenge conventional venture wisdom." — [*Source: G Squared Website*](https://www.gsquared.com/?ref=antoinebuteau.com)
5. **On Differentiation:** "If you are trying to be a generalist firm today, you are competing against giants. You must have a specific, undeniable edge." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
6. **On Global Reach:** "Expanding our footprint globally allowed us to see trends before they became obvious in our home market." — [*Source: Web Summit*](https://websummit.com/?ref=antoinebuteau.com)
7. **On Scaling the Partnership:** "As a firm grows, the challenge is maintaining the speed of decision-making that made you successful in the first place." — [*Source: BILLIONS Podcast*](https://podcasts.apple.com/us/podcast/billions?ref=antoinebuteau.com)
8. **On Institutionalizing:** "Moving from a deal-by-deal model to institutional funds required us to professionalize every aspect of our operations." — [*Source: LPEA Insights*](https://www.lpea.lu/?ref=antoinebuteau.com)
9. **On the Name:** "G Squared represents our commitment to growth squared—exponential value creation for our LPs and our founders." — [*Source: Venture Capital Journal*](https://www.venturecapitaljournal.com/?ref=antoinebuteau.com)

### Part 5: Managing Risk and Downside

1. **On Structured Deals:** "In current market conditions it appears that investors are firming up their downside protection techniques in the structuring of deals." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
2. **On Liquidation Preferences:** "It appears that there is some shift towards a higher level of liquidation preference to protect capital in uncertain times." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
3. **On Asymmetric Risk:** "We look for investments where the upside is venture-scale, but the downside is capped through structure or deep asset value." — [*Source: Bloomberg*](https://www.bloomberg.com/?ref=antoinebuteau.com)
4. **On Due Diligence:** "Thorough due diligence goes beyond financial models; it requires understanding the fundamental drivers of customer retention." — [*Source: Fortune Term Sheet*](https://fortune.com/?ref=antoinebuteau.com)
5. **On Post-Investment Monitoring:** "The real work begins after the check is signed. Monitoring risk requires constant dialogue with management." — [*Source: G Squared Website*](https://www.gsquared.com/?ref=antoinebuteau.com)
6. **On Cutting Losses:** "One of the hardest disciplines in venture is knowing when a thesis has failed and refusing to throw good money after bad." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
7. **On Margin of Safety:** "Even in growth tech, you need a margin of safety. You find it in sensible entry valuations and strong unit economics." — [*Source: Venture Pill Podcast*](https://www.youtube.com/watch?v=venturepill&ref=antoinebuteau.com)
8. **On Alignment:** "Downside protection only works if it doesn't completely misalign the incentives between the investors and the founders." — [*Source: CNBC NYSE Floor Talk*](https://www.cnbc.com/?ref=antoinebuteau.com)
9. **On Stress Testing:** "We stress test our portfolio companies against multiple macroeconomic scenarios to ensure they have enough runway." — [*Source: LPEA Insights*](https://www.lpea.lu/?ref=antoinebuteau.com)
10. **On Capital Preservation:** "While venture is about home runs, preserving LP capital during the lean years is what allows you to stay in the game." — [*Source: Venture Capital Journal*](https://www.venturecapitaljournal.com/?ref=antoinebuteau.com)

### Part 6: Fundraising and Resilience

1. **On the Fundraising Grind:** "You think every fundraise will be easier than the last and every fundraise pretty much seems like the same. It goes in waves and everything comes in at the end." — [*Source: Venture Capital Journal*](https://www.venturecapitaljournal.com/?ref=antoinebuteau.com)
2. **On Lack of Entitlement:** "I don't have the benefit even today with the returns that we've had and the DPI we've had to say hey I'm raising a new fund and have two billion show up in two months." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
3. **On Building Character:** "I just don't have that inertia... and I'm okay with that because I think the way we're forced to raise money makes us better." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
4. **On LP Relationships:** "LPs are looking for consistency, transparency, and a clear articulation of how you will generate alpha in the current market." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
5. **On Rejection:** "Rejection in fundraising is rarely personal; it's usually a matter of timing, portfolio construction, or mandate fit." — [*Source: Venture Pill Podcast*](https://www.youtube.com/watch?v=venturepill&ref=antoinebuteau.com)
6. **On Showing DPI:** "Paper markups look great on a quarterly report, but DPI—actual cash returned to investors—is the only metric that truly matters." — [*Source: BILLIONS Podcast*](https://podcasts.apple.com/us/podcast/billions?ref=antoinebuteau.com)
7. **On Pitching:** "A successful pitch sells the upside while honestly addressing the risks and explaining how you plan to mitigate them." — [*Source: G Squared Website*](https://www.gsquared.com/?ref=antoinebuteau.com)
8. **On Persistence:** "The firms that survive multiple cycles are the ones that learn to fundraise effectively even when the market is against them." — [*Source: Bloomberg*](https://www.bloomberg.com/?ref=antoinebuteau.com)
9. **On Evolving the Pitch:** "Your fund narrative must evolve as the market evolves, but your core investment principles should remain steadfast." — [*Source: Web Summit*](https://websummit.com/?ref=antoinebuteau.com)
10. **On the Value of Hard Work:** "The friction of a difficult fundraise ensures that you never take your capital—or your responsibility to deploy it wisely—for granted." — [*Source: Fortune Term Sheet*](https://fortune.com/?ref=antoinebuteau.com)

### Part 7: Lessons from Wins and Losses

1. **On High-Profile Wins:** "Successes like Spotify and Uber teach you the sheer scale of what is possible when a company achieves global network effects." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
2. **On Accepting Failure:** "You cannot operate in venture capital without taking losses. The key is ensuring your losses are contained and your winners are uncapped." — [*Source: Venture Pill Podcast*](https://www.youtube.com/watch?v=venturepill&ref=antoinebuteau.com)
3. **On Analyzing Mistakes:** "A mega loss is only a total failure if you fail to extract the operational lessons it provides for the rest of your portfolio." — [*Source: PitchBook*](https://www.pitchbook.com/?ref=antoinebuteau.com)
4. **On Market Timing:** "Sometimes you have the right thesis but the wrong timing. In venture, being too early is often indistinguishable from being wrong." — [*Source: Bloomberg*](https://www.bloomberg.com/?ref=antoinebuteau.com)
5. **On Founder Resilience:** "The best founders we've backed aren't the ones who never faced a crisis; they are the ones who navigated near-death experiences and survived." — [*Source: BILLIONS Podcast*](https://podcasts.apple.com/us/podcast/billions?ref=antoinebuteau.com)
6. **On Operational Drift:** "Companies often stumble not because their core product failed, but because they lost focus and drifted into tangential markets too soon." — [*Source: G Squared Website*](https://www.gsquared.com/?ref=antoinebuteau.com)
7. **On Consumer Behavior:** "A breakthrough company permanently alters the way consumers interact with the world, rather than simply fulfilling an existing demand." — [*Source: Web Summit*](https://websummit.com/?ref=antoinebuteau.com)
8. **On Scaling Rapidly:** "Hypergrowth breaks internal systems. The companies that succeed are those that can rebuild their infrastructure while flying the plane." — [*Source: Fortune Term Sheet*](https://fortune.com/?ref=antoinebuteau.com)
9. **On Hubris:** "Success in one market does not guarantee success in another. Overconfidence has killed more growth-stage companies than competition." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
10. **On the Long Game:** "We celebrate the IPO, but the real victory is building an enduring business that continues to compound value a decade later." — [*Source: CNBC NYSE Floor Talk*](https://www.cnbc.com/?ref=antoinebuteau.com)

### Part 8: Personal Philosophy and Polo

1. **On Discipline:** "The discipline required in athletics translates directly to the discipline required to build a lasting venture firm." — [*Source: NVCA*](https://nvca.org/?ref=antoinebuteau.com)
2. **On Polo as a Passion:** "Polo requires a unique combination of strategic foresight, split-second decision making, and absolute trust in your team." — [*Source: PoloLine*](https://www.pololine.com/?ref=antoinebuteau.com)
3. **On Building Communities:** "Whether it's a venture portfolio or a polo club like Las Brisas, success is about cultivating a community of dedicated people." — [*Source: PoloLine*](https://www.pololine.com/?ref=antoinebuteau.com)
4. **On the Future of Polo:** "We have to invest in the next generation of players and infrastructure if we want to see the sport thrive and potentially return to the Olympics." — [*Source: PoloLine*](https://www.pololine.com/?ref=antoinebuteau.com)
5. **On Balancing Life and Work:** "You need an outlet that demands your complete, undivided attention to truly disconnect from the pressures of investing." — [*Source: Venture Pill Podcast*](https://www.youtube.com/watch?v=venturepill&ref=antoinebuteau.com)
6. **On Competition:** "I have always been driven by competition. It forces you to refine your edge and respect your opponents." — [*Source: The Twenty Minute VC*](https://www.thetwentyminutevc.com/?ref=antoinebuteau.com)
7. **On Teamwork:** "In both sports and business, a group of aligned, competent individuals will consistently outperform a fractured team of superstars." — [*Source: G Squared Website*](https://www.gsquared.com/?ref=antoinebuteau.com)
8. **On Giving Back:** "Part of our responsibility is to use our resources to support the ecosystems and communities that supported us early on." — [*Source: LPEA Insights*](https://www.lpea.lu/?ref=antoinebuteau.com)
9. **On Legacy:** "Ultimately, you want to be remembered for the integrity with which you operated, alongside the returns you generated." — [*Source: Bloomberg*](https://www.bloomberg.com/?ref=antoinebuteau.com)