Visual summary of operating lessons from Larry Aschebrook.

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
  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
  3. On Market Maturation: "The secondary market has evolved from a niche strategy into a core function within venture capital." — Source: Venture Capital Journal
  4. On Founders' Needs: "Founders need options to reward early employees without being forced into a premature public offering." — Source: The Twenty Minute VC
  5. On Structural Shifts: "Companies are reaching massive scale while still private, fundamentally changing where the wealth creation happens." — Source: PitchBook
  6. On Price Discovery: "Secondary transactions provide vital price discovery in a market that can otherwise remain opaque for years." — Source: Bloomberg
  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
  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
  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

Part 2: Venture Capital Strategy

  1. On Precision: "We fire a rifle to calibrate a cannon ball." — Source: Venture Capital Journal
  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
  3. On Evaluating Companies: "We look for companies that have achieved scale and fundamentally changed consumer behavior." — Source: CNBC NYSE Floor Talk
  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
  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
  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
  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
  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
  9. On Deal Sourcing: "The best deals often come from long-term relationships built years before a transaction ever takes place." — Source: LPEA Insights

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
  2. On Valuations: "Valuations are cyclical, but intrinsic value is built steadily over time regardless of the macroeconomic environment." — Source: Bloomberg
  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
  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
  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
  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
  7. On Volatility: "Volatility creates opportunity for secondary buyers who have the conviction to step in when others are stepping back." — Source: BILLIONS Podcast
  8. On Patience in Bear Markets: "The best vintages in venture capital are often deployed during the most pessimistic market environments." — Source: PitchBook
  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

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
  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
  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
  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
  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
  6. On Global Reach: "Expanding our footprint globally allowed us to see trends before they became obvious in our home market." — Source: Web Summit
  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
  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
  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

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
  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
  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
  4. On Due Diligence: "Thorough due diligence goes beyond financial models; it requires understanding the fundamental drivers of customer retention." — Source: Fortune Term Sheet
  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
  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
  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
  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
  9. On Stress Testing: "We stress test our portfolio companies against multiple macroeconomic scenarios to ensure they have enough runway." — Source: LPEA Insights
  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

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
  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
  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
  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
  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
  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
  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
  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
  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
  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

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
  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
  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
  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
  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
  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
  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
  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
  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
  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

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
  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
  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
  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
  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
  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
  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
  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
  9. On Legacy: "Ultimately, you want to be remembered for the integrity with which you operated, alongside the returns you generated." — Source: Bloomberg