What does it take to recruit the top 0.1% of engineers in the world — and why has talent become the ultimate constraint in AI? In this episode, I’m joined by Chris Vasquez, Founder & CEO of Quantum Talent, one of the most in-demand technical recruiting firms in the AI ecosystem. We discuss why elite engineering talent has become the core bottleneck in AI, how companies can actually attract S-tier builders, what founders get wrong about hiring, and why talent density—not headcount—is the strongest predictor of outcomes in today’s startup environment.

Highlights:

• Why AI founders are “at war” — and recruiting firms are the arms dealers. Defining S-tier talent: clear evidence of greatness, spiky abilities, and proven complexity-handling.
• Capital is abundant; talent is the true constraint in modern AI company building.
• Why companies must tell a compelling story if they lack high-signal founders or top-tier backers.
• How AI’s rapid improvement reshapes recruiting needs — fewer engineers, but far more specialized ones.
• The Sequoia-backed company that failed to hire until they raised their comp bands. (7 declines vs. 17 hires after fixing comp.)
• Why founders should overpay strategically for the roles that matter most.
• Key signals elite engineers look for: founding team quality, investor pedigree, mission clarity, and market upside.
• Why “experience with greatness” de-risks execution in early-stage teams.
• The #1 heuristic Chris wishes he learned earlier: “If you wouldn’t hire 100 of that person, don’t hire one.”

Guest Bio:

Chris Vasquez is the Founder & CEO of Quantum Talent, a specialized recruiting firm focused on placing elite technical talent into leading AI, frontier-tech, and enterprise software startups. Quantum works with hundreds of venture-backed companies and has partnered with 80% of Tier 1 VC firms, helping founders build high-density engineering teams capable of shipping breakthrough products.

With deep expertise in identifying the top 0.1% of engineers, researchers, and product leaders, Chris and his team have become one of the most trusted upstream partners in the AI ecosystem — operating at the intersection of talent, technology, and high-velocity company building.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Chris Vasquez:

LinkedIn: https://www.linkedin.com/in/chris-vasquez-66137553/ Quantum: https://www.quantumtalent.io/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected]. [email protected].

(0:00) Introduction (2:38) Talent Density and the Shift from Capital to Talent in Startups (5:16) AI's Impact on Talent Recruitment and Compensation Strategies (9:45) What S Tier Engineers Seek in Companies (11:14) Establishing Talent Density by Overpaying Initial Hires (14:28) The Role of Talent in Product-Market Fit (17:21) Strategies for Recruiting Top AI Talent (24:01) The Distinction Between Good and S-tier Recruiters (27:43) Effective Recruiting Heuristics and Compensation Tactics (30:23) Managing Internal Politics for High Compensation Hires (31:48) Timeless Advice for Recruiters (34:34) Closing remarks

How do you balance power-law outcomes with real risk management while building a durable venture franchise? In this episode, I speak with Mark Peter Davis (MPD) — Managing Partner of Interplay, entrepreneur, author, podcaster, and one of New York’s most active early-stage investors. We discuss how Mark’s philosophy of investing has evolved over 20 years in venture, why VC psychology is so different from other asset classes, and how he manages for both outliers and consistency across vintages. Mark breaks down secondaries, constructing high-access portfolios, founder relationships, narrative risk, the role of operational support, and why grit compounds just like interest.

Highlights:

• How 20 years in venture reshaped Mark’s thinking on risk, liquidity, and exit timing.
• Why early VCs get caught in the “TechCrunch punch” and over-index on hope.
• Power laws vs. portfolio consistency — why vintages swing and how Mark mitigates volatility.
• How secondaries, tenders, and mid-market PE can drive liquidity for the “middle 80%” of winners.
• The “tweener rule”: why Interplay often sells ~50% when outcomes are unclear.
• Incentive alignment between GPs and LPs — and why building a long-term institution changes behavior.
• Avoiding narrative traps: why founder behavior and fund construction matter more than storytelling.
• Brokerage-model VC vs. operational-institutional VC — and why the difference is huge.
• How soft commits, goodwill, and reference strength drive proprietary access.
• Entrepreneurship patterns: the “500 problems” every startup faces.
• Why you can’t learn entrepreneurship in a classroom — only through reps.
• The compounding effect of grit and staying in the game long enough.

Guest Bio:

Mark Peter Davis is a venture capitalist, serial entrepreneur, author, and startup community organizer.

MPD is the Managing Partner of Interplay, a startup ecosystem based in NYC that supports founders and innovation at every stage. The ecosystem comprises a top-performing venture capital fund, an accelerator, a studio, a services platform, and a multi-family office. With over 100 companies funded, incubated, or founded, he ranks among the most active startup founders and investors in New York City.

MPD is also an active podcaster, the author of The Fundraising Rules, and the founder of both the Columbia Venture Community and the Blue (Duke) Venture Community.

Prior to his current ventures, MPD was a venture capitalist at DFJ Gotham Ventures and Primary Ventures. Before entering VC, he was a M&A advisor to Fortune 1000 acquirers at KPMG and a strategy and operations consultant at Bain & Company.

MPD earned his BA from Duke University and his MBA from Columbia Business School.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#venturecapital #vc #startupsuccess #openlp #assetmanagement

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Mark Peter Davis:

LinkedIn: https://www.linkedin.com/in/markpeterdavis/ X/Twitter: https://x.com/mpd Interplay: http://interplay.vc/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected]. [email protected].

(0:00) Introduction (0:31) Evolution and counterintuitive lessons in venture investing (3:25) Reconciling investment worldviews and managing liquidity (7:35) Decision-making and aligning VC incentives with LP interests (12:03) Building an enduring institution and measuring success (18:07) Achieving access to competitive deals and proprietary deal flow (24:24) Competitive tension's impact on investment support (27:19) Integrity and resources in VC partnerships (30:02) Entrepreneurial experience's value in venture capital (32:24) Startups' challenges and the role of pattern recognition (35:24) Unlearning and cognitive restructuring in entrepreneurship (37:23) Mastering the complexities of long-term entrepreneurship (38:11) Timeless advice for aspiring entrepreneurs and enduring success (41:51) Closing remarks

How do the best family offices consistently spot power-law opportunities and avoid the trap of “fake busy” work? In this episode, I’m joined with William (Bill) Brown, CIO of the Terrace Tower Group, about the lessons he learned working for billionaire Leonard Stern, how he helped evolve a legacy real-estate portfolio into a globally diversified family office, and what pattern recognition looks like across trades like the Big Short, crypto, and private credit. We discuss how Bill thinks about decision-making, mental models, productivity, and the mindset required to survive long enough to capture asymmetric upside.

Highlights:

• Lessons from working under Leonard Stern — focus on what truly matters.
• Why “don’t confuse activity with progress” became a lifelong principle.
• How Stern gathered insights by walking the office and challenging ideas in real time.
• The importance of taking leaders on a journey, not presenting decisions once.
• Batting average vs. slugging percentage — finding your investing style. (Ichiro vs. Aaron Judge)
• Behind the scenes of the Big Short trade — identifying early signals.
• Navigating months of drawdowns and conviction challenges.
• How to know whether you’re the “dumbest person in the room” and avoid confirmation bias.
• Why the best ideas often come from “other herds” and cross-network pattern recognition.
• Crypto pattern recognition — spotting the signal when two very different founders agree.
• How Terrace Tower built a diversified global portfolio from a real-estate foundation.
• Using private credit to replace income after a major asset sale. “Fake busy” vs. deep work — designing days for real thinking.
• Staying in the game long enough to benefit from power-law outcomes.

Guest Bio:

William “Bill” Brown is the Chief Investment Officer of Terrace Tower Group, a global family office originating from the Westfield legacy. Bill oversees the group’s non-real-estate portfolio, spanning public equities, private equity, venture capital, and private credit. Before joining Terrace Tower in 2010, Bill worked in investment banking and spent his early career at Salomon Brothers. His investing philosophy is shaped by decades of experience working with the Stern family and managing multi-asset portfolios across cycles.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#VentureCapital #VC #Startups #OpenLP #AssetManagement

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Bill Brown:

LinkedIn: https://www.linkedin.com/in/william-brown-1a48593/ Terrace Tower Group: https://www.ttgroup.co/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected]. [email protected].

(0:00) Introduction (0:12) Leonard Stern's investment philosophy and unique work habits (2:16) Leonard Stern's idiosyncratic bets and discussion on risk (4:49) Jeff Bezos and asymmetry in business (5:23) Introduction to and expansion of the big short trade (13:30) Evaluating complex trades as a family office (15:18) Cultivating the right investment mindset (18:53) Early investments in crypto and avoiding busy work (23:02) Energy management and strategic networking (25:10) The importance of not overthinking and perfection in investing (27:03) Resisting the temptation to sell too early (29:13) The importance of staying in the game and imagination in investing (33:19) Terrace Tower Group's current focus and portfolio execution (42:02) Advice for younger self and focusing on what matters (46:42) Closing remarks

How do you scale from a $10M first fund to managing over $1.5B — all in one of the most capacity-constrained asset classes on earth? In this episode, I talk with Eva Shang, Co-founder and General Founder of Legalist, about dropping out of Harvard, getting into Y Combinator, pivoting from legal analytics to litigation finance, and raising their first $10M fund long before they had any track record. We discuss why Legalist chose the fund model over the venture-backed originator model, how they deployed their algorithm to find late-stage cases at scale, why litigation finance is capacity constrained, and how Legalist expanded into adjacent strategies like bankruptcy, mass torts, law-firm lending, and government receivables.

Highlights:

• How Legalist began as a data-driven legal-analytics platform.
• Why the team shifted from software to asset management.
• How technology identifies litigation, bankruptcy, and receivables opportunities.
• The role of public-records sourcing and automated case screening.
• Why Legalist focuses on uncorrelated, niche credit strategies.
• How Legalist evaluates risk in litigation finance.
• How the team structures underwriting across legal and credit factors.
• Why government receivables and bankruptcy claims require specialized processes.
• How Legalist works with law firms, claimants, and contractors.
• Eva’s philosophy on building teams, culture, and long-term systems.

Guest Bio:

Eva Shang is the Co-founder and General Partner of Legalist, an asset manager specializing in technology-enabled investments across litigation finance, bankruptcy, law-firm lending, mass torts, and government receivables. Eva co-founded the firm in 2016 after leaving Harvard and entering Y Combinator, and has led Legalist from its $10M debut fund to over $1.5B in AUM across multiple strategies.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#venturecapital #vc #startups #openlp #assetmanagement

Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Eva Shang: LinkedIn: https://www.linkedin.com/in/eshang/ Legalist: https://www.legalist.com/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Introduction (2:20) Y Combinator insights and venture capital decisions (4:51) Emphasizing IRR in building a sustainable business model (6:48) Lessons from early fundraising and growth strategies (9:36) Diversification and understanding capacity-constrained assets (13:33) Fundamentals of litigation finance and sources of alpha (18:08) Exploring the government receivables strategy (20:38) Cultivating long-term vision and independent mindedness in entrepreneurship (24:33) Reflecting on past decisions and the importance of team building (26:14) Closing remarks

What does it actually take for an emerging manager to convince a top LP to invest? In this episode, I’m joined by Alex Edelson, Founder of Slipstream, and one of the most respected LPs backing elite seed funds today. Alex pulls back the curtain on how LPs use AI, what “real talk” references look like, how he evaluates GPs, and why only a tiny percentage of funds ever make it through his screening. We also dive into portfolio construction, picking and winning founders, why deep tech requires more shots on goal, and how Alex builds long-term trust with the world’s top institutions. This conversation is a masterclass in LP underwriting and what separates good managers from truly exceptional ones

Highlights:

• How top seed funds use AI for sourcing, diligence, and market research.
• Why underwriting venture still comes down to relationships, brand, and founder trust.
• Why Slipstream screens out ~95% of funds before doing references.
• What “real talk references” reveal that most LPs never hear.
• Why deep tech sometimes needs more shots on goal with slightly lower ownership.
• How Alex developed his “right to win” as an LP after QED.
• What GPs misunderstand about the bar for raising today.
• How anti-selling helps LPs filter for long-term partners.
• Why LP relationships often become deep personal relationships over time.
• The frontier of the next decade: AI-driven investing and pre-consensus founder identification.

Guest Bio:

Alex Edelson is the Founder of Slipstream, an LP firm focused on backing top early-stage venture funds. Before launching Slipstream, Alex was part of the leadership team at QED Investors, where he helped shape their approach to portfolio construction, fund strategy, and LP engagement. His legal background and deep relationships across the founder/VC ecosystem have made him one of the most sought-after LP partners for emerging and established seed GPs.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#VentureCapital #VC #Startups #OpenLP #AssetManagement

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alex Edelson: https://www.linkedin.com/in/alex-edelson-604767b/

Links Slipstream Investors: https://www.slipstreaminvestors.com/ Weisburd Capital: https://www.weisburdcapital.com/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Introduction (0:06) Seed funds, AI usage, and diligence processes (1:56) Growing prominence of AI and unique investment approaches (4:00) Constructive GP conversations and Slipstream's strategy (6:11) Comparisons to Palantir and investment beliefs (8:07) Differing views on identifying good GPs (10:55) The importance and role of references in diligence (19:04) Screening out funds and challenges for emerging managers (25:49) Attracting top LPs and building relationships (30:03) The concept of antiselling and excitement for the future (35:17) Closing remarks

What does it really take to raise a venture fund—and why does fundraising never get easier, even at Fund 5 or Fund 6? In this episode, I talk with Yasmine Lacaillade, Founder of Sinefine and one of the most respected capital formation leaders in venture. Yasmine shares her journey from TPG Axon in London to joining Drive Capital at Fund I—years before it became consensus. We discuss why fundraising is always difficult, how LP sentiment shifts every 2–3 years, and why top fundraisers treat the process like enterprise sales rather than relationship maintenance. Yasmine breaks down her market mapping framework, why the top of the funnel must always stay wide, how to qualify LPs quickly, and why “adding value first” is her core operating principle. She also explains how she evaluates new managers, how to identify true LP demand today, and why people, culture, and team cohesion matter more than anything else in venture.

Highlights:

• How moving from London to Columbus led Yasmine into the earliest days of Drive Capital.
• Why she joined Drive at Fund I—and what she saw before LPs did.
• Why fundraising never gets easier, even after multiple successful vintages.
• How LP priorities, liquidity, and macro cycles shift every 2–3 years.
• The difference between networking vs. honing existing relationships.
• Why Yasmine treats fundraising like enterprise sales—and why a huge top of funnel is essential.
• What LPs are actually looking for in a first meeting
• How to qualify LPs quickly by asking exactly what they’ve invested in over the last 6–12 months.
• Why the most important skill in fundraising is mapping the market and respecting LPs’ time.
• How Sinefine structures a new engagement with a GP—from deck narrative to LP segmentation.
• Why she only works with a handful of managers and how she selects them.
• How she evaluates team cohesion and founder intensity
• Why her philosophy is to add value before asking for anything.
• The psychology of transactional vs. non-transactional relationships and the idea of “goodwill reservoirs.”
• Why she shut down her fund-of-funds product and how she built Sinefine into a product-oriented platform.
• How Zoom culture has changed LP behavior, time allocation, and transparency.
• The importance of story evolution, narrative sharpening, and portfolio math in venture.

Guest Bio:

Yasmine Lacaillade is the Founder of Sinefine, a capital formation and institutional fundraising advisory firm working with top-tier venture managers. Before launching Sinefine, Yasmine spent over a decade in investment and fundraising roles, including at TPG Axon in London and as an early team member at Drive Capital, where she helped build one of the leading venture franchises in the Midwest from its first fund onward. Yasmine specializes in market mapping, LP strategy, investor relations, and helping emerging and established GPs navigate complex fundraising environments. She is widely recognized for her clarity of thinking, LP intelligence, and ability to guide managers through the entire capital formation journey.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#VentureCapital #VC #Startups #OpenLP #AssetManagement

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Yasmine Lacaillade: https://www.linkedin.com/in/yasmine-lacaillade-6448888/

Links Sinefine: https://www.sinefine.co/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Introduction (3:08) Fundraising challenges in venture capital vs. hedge funds (5:00) Networking and managing relationships in fundraising (9:12) Balancing relationships with the transactional nature of fundraising (13:22) Market mapping and targeting LPs effectively (17:02) Long-term investment decisions and adapting to market conditions (21:58) Building trust in first meetings with LPs (27:36) Transactional relationships and adding value in LP-GP dynamics (31:08) Onboarding a new fund and quick trust-building (34:44) Pursuing relationships with potential managers and the Ashton Kutcher investing principle (38:45) Balancing personal and professional commitments (40:06) Embracing people-pleasing as a strength in investing (42:49) Reputation and value creation in the investment world (44:31) Passion for venture capital and finding excitement in buyouts (49:30) Team cohesion and investment success (50:09) Closing

How do LPs unlock liquidity from private-fund positions without selling at a discount? In this episode, I talk with Alex Simpson, Co-founder of Liquid LP, a platform that provides NAV loans backed by LP and GP interests in private funds. Alex explains how NAV loans work, how lenders underwrite illiquid portfolios, and when borrowing may be preferable to selling in the secondary market. We also discuss how different types of investors—high-net-worth individuals, family offices, and institutions—use these loans for personal liquidity, capital calls, tax needs, portfolio rebalancing, or simply as a liquidity backstop. We also cover underwriting, LTV ranges, recourse structures, timing, advisory boards, and the origin story behind Liquid LP.

Highlights:

• What a NAV loan is and how LP interests serve as collateral.
• Why some LPs choose a NAV loan rather than selling at a discount.
• How high-net-worth investors use NAV loans for personal liquidity and taxes.
• How institutions use NAV loans for portfolio management and capital calls.
• Differences between Liquid LP and large banks like J.P. Morgan or Goldman Sachs.
• Underwriting approach: fund quality, diversification, existing pledges, and use of proceeds.
• Typical LTV ranges (approx. 20–40%) depending on underlying collateral.
• Loan pricing drivers: asset quality, diversification, and loan structure.
• Loan timelines: from fast two-week processes to more complex multi-week cases.
• Recourse vs. non-recourse structures and when each applies.
• Why purpose of the loan matters for underwriting, even if terms are asset-driven.
• Standby NAV lending partnerships with funds to support LP liquidity.
• How GPs sometimes use loans to bridge GP commitments when DPI is slow.
• How Alex built Liquid LP, beginning with pre-IPO lending before shifting to LP liquidity solutions.
• Key risks in NAV lending: undisclosed pledges, documentation issues, and thin data on smaller funds.
• Lessons learned from building an advisory board and aligning incentives.

Guest Bio:

Alex Simpson is the Co-founder of Liquid LP, a fintech platform that provides NAV-backed lending solutions for LPs, GPs, family offices, and wealth-management clients. Before founding Liquid LP, Alex built and operated companies in South Africa and Australia and worked closely with executives at late-stage and pre-IPO technology companies. His experience in private markets, lending, and alternative-asset liquidity led him to develop a platform focused on helping investors access liquidity without selling long-term positions.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexander Simpson: https://www.linkedin.com/in/alsimpson1/

Links LiquidLP: https://www.linkedin.com/company/liquidlps/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Introduction (1:07) Scale of operations, target clientele, and market rates (2:29) Use cases for institutions and competition with large banks (4:04) Due diligence and factors influencing loan terms (8:15) Recourse vs nonrecourse loans and loan's purpose (10:37) NAV loans for investment stability and GP commit solutions (12:46) Flexibility and risk assessment in lending (15:07) Loan durations, processing times, and standby partnerships (18:22) GP stakes field and LiquidLP's origin and evolution (21:04) NAV loan risks and managing an advisory board (24:34) Advisory board strategy and balancing impact with finance (27:52) Company culture, leveraging finance for impact, and unifying principles (34:25) Closing remarks

What makes a GP interest valuable — and how do you evaluate a manager beyond the fund they’re raising today? In this episode, I talk with Mark Wade, CAIA, Partner at CAZ Investments, about how his team assesses GP interests, private-market managers, partnership structures, and long-term durability. We discuss why GP transactions have evolved, why some firms seek outside capital, and the practical differences between investing as a GP versus an LP. We also touch on evaluating leadership succession, LP base diversification, liquidity considerations, and why sports franchises continue to attract investor interest.

Highlights:

• How GP interest transactions have changed over the past decade.
• Why private-market firms seek external capital to support growth.
• Key differences in evaluating a GP interest versus an LP fund commitment.
• What CAZ looks for in partnership stability and leadership succession.
• How LP base diversification factors into long-term durability.
• Liquidity considerations and how secondary/tender processes work.
• Why sports franchises attract investor attention and how league structures differ.

Guest Bio:

Mark Wade is a Partner at CAZ Investments, where he leads investment strategy and firm initiatives. Since joining CAZ in 2013, Mark has helped the firm expand its presence across asset classes, with a particular focus on GP stakes, energy, and professional sports. Prior to CAZ, Mark earned his MBA from the University of Chicago Booth School of Business. CAZ is known for its alignment-first model—deploying more than $700 million of insider capital alongside its LPs across a range of alternative investments.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#VentureCapital #VC #Startups #OpenLP #AssetManagement

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mark Wade: https://www.linkedin.com/in/mark-wade-caia-334b951b/

Links CAZ Investments: https://cazinvestments.com/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected]

(0:00) Introduction (0:14) Mark Wade's background and focus on private markets (2:14) Structuring and capital needs in GP stakes investments (7:15) Key considerations and differences in GP stakes vs LP investments (11:24) Downside protection and alignment of interests in GP stakes (15:01) Base case expectations and liquidity concerns in GP stakes (19:39) Sports investments discussion and value growth (24:15) Comparing sports investments to Bitcoin and impact of AI (25:07) Future trends and investing focus in sports entertainment (26:08) Closing remarks

Is traditional valuation dead for the biggest winners of the AI era? Or have investors simply been looking in the wrong place? In this episode, I talk with Dan Ives, Managing Director and Global Head of Technology Research at Wedbush Securities, and one of Wall Street’s most followed tech analysts. Dan has covered the software and technology sector for 25 years, becoming known for his bold, high-conviction calls on Tesla, Nvidia, Microsoft, and Palantir long before they became consensus. We break down why Dan calls Tesla the world’s leading “physical AI” company, why he thinks AI is the largest tech transformation in 40–50 years, what investors miss when they rely only on spreadsheets, and how his pattern-recognition framework helps him spot multi-baggers years before the herd.

Highlights:

• Why he views Tesla far beyond autos; autonomy, robotics, robo-taxis, and multi-trillion-dollar upside.
• Why he believes AI is a 40–50 year mega-cycle with second- and third-order winners.
• Why do great companies look expensive every year until suddenly they don’t.
• On pattern recognition, global customer conversations, and signals that never show up in models.
• Lessons from 2008, 2022, and sticking with calls through volatility.
• Why Nadella, Musk, Karp, and Lisa Su are misunderstood and mispriced by Wall Street.
• His 1–10 conviction framework and how he sizes up when inflection happens.
• Where he’s looking for the next multi-baggers in the AI supply chain.
• How setbacks early in his career reshaped his investing worldview.
• His role as Chairman of ORBS (EightCo Holdings) and Worldcoin-aligned authentication.
• Why he partnered with Snow Milk on a fashion collaboration and how “owning who you are” fuels differentiation.

Guest Bio:

Daniel Ives is the Managing Director and Global Head of Technology Research at Wedbush Securities, where he has been a senior equity research analyst covering the technology sector since 2018. Dan has spent 25 years on Wall Street following software, cloud, cybersecurity, mobile, and the broader enterprise tech ecosystem.

He is also the Chairman of EightCo Holdings (ORBS), focused on authentication and digital identity infrastructure aligned with the emerging AI era.

Dan is one of the most sought-after tech experts globally, regularly appearing on CNBC, Bloomberg, BBC, Fox Business, ABC, NBC, Sky News, France 24, NPR, and many other global outlets. He is frequently cited in The Wall Street Journal, The New York Times, Financial Times, Barron’s, Time, The Telegraph, and other major publications.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#venturecapital #vc #startups #openlp #assetmanagement

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Daniel Ives: https://www.linkedin.com/in/daniel-ives-542321a8/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Preview (1:17) Dan Ives on the AI revolution, Tesla's market dominance, and valuation methodology (5:10) The importance of long-term vision and global insights in tech investing (10:52) The role of retail investors and the impact of market sentiment (14:25) The significance of true believers and early adopters in investments (16:13) Recognizing when an investment thesis is wrong and adjusting strategies (22:32) Investment sizing, portfolio construction, and utilizing customer feedback (26:16) Psychological biases and their effects on investor confidence (27:06) Leveraging social media and conferences for investment insights (28:31) Understanding power law returns and second/third order effects in the market (32:20) Evaluating investment success: hit rates and the role of outliers (34:09) Influencing stock narratives and decisions at the board level (37:21) Identifying mispriced founder-led companies and embracing failures (43:41) Dan Ives' personal background and approach to maintaining conviction (47:48) Future projects at Wedbush and personal ventures (49:19) Closing remarks

Is private equity still worth it — or has the industry scaled its way into mediocre returns? In this episode, I talk with Nolan Bean, CFA, CAIA, Chief Investment Officer and Head of Portfolio Management at FEG Investment Advisors, an independent, employee-owned firm advising on $90+ billion in assets for endowments, foundations, healthcare systems, and mission-driven institutions. We dig into the state of OCIOs, interval funds, private equity, and why Nolan believes the lower middle-market still offers the clearest path to real alpha. Nolan also breaks down the coming wave of 401(k) access to private markets, why large-cap buyout is structurally challenged, and how FEG uses a “crisis playbook” to lean into markets without pretending to time them perfectly.

Highlights:

• How FEG advises on $90B+ across 300+ clients, mostly nonprofits.
• OCIO incentives, risk-taking, and why some firms drift toward being too conservative.
• Interval funds: easy access, hidden liquidity risks, and “Hotel California” redemptions.
• Why large buyout PE faces pressure from high entry multiples, rates, and too much capital.
• Why lower middle-market buyout still works: founder-led deals, ops value-add, less leverage.
• Main risks in small companies: fragility, client concentration, and key-person exposure.
• Factor models vs. real alpha: where Fama-French stops explaining PE returns.
• Shrinking small-cap universe and why public markets may have adverse selection.
• The coming 401(k) and retail flow into alternatives — and shrinking illiquidity premia.
• FEG’s VFS (valuation, fundamentals, sentiment) crisis framework for drawdowns.
• Four key risks: goal risk, market risk, illiquidity risk, and maverick risk.
• Nolan’s top two lessons: don’t fight the Fed, and relationships compound.

Guest Bio:

Nolan Bean is the Chief Investment Officer and Head of Portfolio Management at FEG Investment Advisors, where he has worked since 2004. He leads portfolio construction, research oversight, and investment strategy across FEG’s OCIO and advisory clients. Nolan is both a CFA and CAIA charterholder. He holds a finance and quantitative analysis degree and an MBA from the University of Cincinnati.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#venturecapital #vc #startups #openlp #assetmanagement

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Nolan Bean: https://www.linkedin.com/in/nolanbean/

Links FEG Investment Advisors: https://www.feg.com/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Introduction (0:28) Growth catalysts and criteria for RIAs and investment advisors (2:13) Criticisms of OCIOs and conservative risk-taking (3:59) Discussion on interval funds and private equity buyouts in 2025 (7:39) Challenges in large buyout funds and lower middle market opportunities (16:23) Risks and benchmarking in lower middle market investments (21:45) Democratization of private markets and 401(k) investments (24:36) Illiquidity premium and institutional investors' response (27:06) Identifying opportunities in out-of-favor sectors and portfolio construction (31:07) Managing risk tolerance and market downturn strategies (34:24) Behavioral finance and liquidity in portfolio management (37:18) Evaluating hedge funds and strategies for market downturns (41:21) Diversification benefits and long-term market trends (44:03) Public policy influence on markets and timeless investment advice (47:55) Interest rates' impact on asset prices and politicians' market influence (53:14) Investing during crises and the importance of relationships (56:18) Venture capitalists, reciprocity, and value in relationships (58:22) Closing remarks

How do you build a multibillion-dollar company from scratch, walk away at the peak, and reinvent your life around purpose, generosity, and impact? In this episode, I talk with Pete Kadens, one of America’s most respected first-generation wealth creators and one of the leading philanthropists focused on closing education and opportunity gaps across the U.S. Today. Pete and I dive into how he built Green Thumb Industries (GTI) into a multibillion-dollar cannabis company, the unsexy strategies that made it work, and why choosing overlooked markets and consumers unlocked massive profit. We cover the power of ownership cultures, transparency, discipline frameworks, and why giving equity and education to employees creates extraordinary performance. We also explore the character transformation that led him to retire at 40.

Highlights:

• The unsexy strategy behind scaling GTI into a multibillion-dollar operator
• Why Pete targeted the 30–50-year-old female consumer long before the market noticed
• How choosing Toledo instead of Chicago and Erie instead of Philadelphia created monopolistic advantages
• The power of ownership cultures, ESOP-style alignment, and financial transparency
• Why employees perform better when they are treated like owners
• Pete’s shift from business success to a life of impact and philanthropy
• The emotional toll, guilt, and clarity that led him to retire at 40
• How he rebuilt his parenting philosophy: presence, character, and modeling discipline
• Why “how you do anything is how you do everything” became his family standard
• The timeless rule he lives by: the gap between “I should” and “I did”

Guest Bio:

Pete Kadens is a serial entrepreneur and dedicated philanthropist who currently serves as Chairman of The Kadens Family Foundation, a national charitable organization focused on closing education and wealth gaps. He is also the Founder and Co-Chairman of Hope Chicago, which is educating tens of thousands of underserved Chicagoans, and a key supporter of Hope Toledo, now serving more than 300 families with tuition-free college and trade-school pathways.

Pete is the Founder & Chairman of Warmer, a new social platform designed to create kind, supportive, and non-toxic peer-to-peer interaction. He also serves as Chairman Emeritus of StreetWise, one of Chicago’s largest homeless assistance organizations, and sits on multiple nonprofit and for-profit boards dedicated to social impact.

Pete is a 2019 Henry Crown Fellow at the Aspen Institute, one of the most selective fellowship programs in the world, recognizing leaders who create ventures solving society’s most challenging problems.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

#venturecapital #vc #startups #openlp #assetmanagement

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Pete Kadens: https://www.linkedin.com/in/petekadens/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Introduction (0:19) Founding Green Thumb Industries and seizing opportunities in the cannabis industry (2:08) Focusing on profit and choosing unsexy locations (4:05) Targeting non-obvious customer segments and building partnerships (7:44) Creating a disciplined framework for employee autonomy and engagement (13:06) The importance and advantages of an employee ownership culture (18:54) Transitioning from business to philanthropy (19:47) Exploring different forms of wealth and personal fulfillment (24:11) Balancing business success with personal life and trade-offs (30:30) Role modeling, parenting philosophies, and teaching kindness (37:40) Pursuing excellence, discipline, and lessons from Aspen Institute fellows (41:41) Importance of suspending assumptions and embracing rest (43:37) Valuing idiosyncratic excellence and embracing neurodivergence (46:28) Turning aspirations into achievements and celebrating progress (49:09) Concept of the minimum lovable product and reflecting on success (50:44) Closing thoughts, gratitude, and how to follow Pete Kadens (51:14) Closing remarks