Jon Staenberg is the founder of Agate Hound Fund, a pioneering institutional fund-of-funds focused on search funds and entrepreneurship through acquisition. A 30-year venture investor, Stanford “trifecta” grad, and longtime small-business owner (from car washes to an Argentine winery), he lives at the intersection of Main Street and Silicon Valley. With decades of pattern recognition across hundreds of angel and VC deals plus deep immersion in ETA, he offers sharp, grounded insights into small business acquisition, operator selection, and what the “silver tsunami” means for ambitious operators and investors.

In this episode, they discuss why boring, profitable businesses might be the most exciting opportunity in the market, how to evaluate 30-something CEOs who’ve never run a company, and why AI plus mom-and-pop America could quietly outperform your favorite tech bets. They also get personal—covering risk tolerance, meditation, travel, and why legacy ultimately comes down to kindness, not cap tables.

Chapters:

00:01 Early Roots in Omaha & First Lessons in Entrepreneurship

04:12 The Stanford Journey and Discovering Venture Capital

07:45 What Search Funds Really Are: A Simple Breakdown

10:18 The “Silver Tsunami” Opportunity in Small Business Ownership

13:32 How Search Funds Differ From Traditional VC Models

17:05 Incentives, Alignment, and Why ETA Produces Steady Returns

20:41 Who Makes a Great Searcher? Traits, Backgrounds & Patterns

24:58 Jon’s 30-Year VC Career and the Shift Toward ETA

29:10 Building a Winery in Argentina: Lessons in Main Street Ops

33:27 Designing a Life With Curiosity, Adventure, and Work

37:14 Compounding Wisdom: Experience, Self-Awareness & Growth

41:52 Meditation as an Operating System for Better Decision-Making

45:36 The Story Behind Agate Hound & Finding “Investment Gems”

48:22 The Biggest Misconceptions About Young ETA Operators

51:03 ETA in a Tech-Driven Future: AI Meets Main Street

53:26 Closing Reflections on Legacy, Kindness & Long-Term Impact

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Max Sinclair is the founder and CEO of Azoma, an AI SaaS company helping global brands win in AI-powered search. A former Amazon product lead, he helped launch Amazon Business in the UK, led search and browse for Amazon Singapore, and headed EU Grocery before jumping into founder life. With deep experience across e-commerce search, item data quality, and now answer engine optimization (AEO), he offers sharp, battle-tested insights into how AI is reshaping product discovery, growth, and go-to-market for enterprise brands. In this episode, he discusses leaving a fast-track Amazon career to join Entrepreneur First, building one of the earliest AEO platforms before the market believed, scaling to seven-figure revenue on inbound alone, and why he thinks today’s bloated media agencies are squarely in AI’s crosshairs.

In Today’s Episode We Discuss:

00:01 Meet Max Sinclair & why AI search is breaking marketing rules

00:28 Max’s Amazon journey: Amazon Business UK, Singapore search, and EU Grocery

01:54 Leaving Amazon for Entrepreneur First and betting early on LLMs in search

03:28 Going contrarian: selling “answer engine optimization” before anyone cared

04:38 SEO vs AEO: how LLMs change the playbook for winning in search

05:04 What “answer engine optimization” actually means for brands

05:50 Taking the plunge: advice for operators thinking about quitting big tech

08:01 Inside Entrepreneur First: matching commercial and technical founders

10:08 Surviving the “too early” phase and riding the AI search inflection

12:14 Are we at product–market fit? How Max thinks about enterprise PMF

14:54 Scaling mostly on inbound: 40–50% monthly growth with no outbound

16:48 The content strategy behind Azoma’s pipeline (and getting over cringe)

18:11 Under the hood: how Azoma simulates ChatGPT-style queries and optimizes answers

20:03 What it looks like as a customer: winning recommendations in answer engines

20:31 The next 1–2 years: hiring spree, category creation, and owning “answer engines”

22:34 Hiring in Europe vs the US and why firing is much harder in the EU

24:42 Remote vs in-person: why Max wants hubs, not fully-remote everywhere

25:29 Long-term bet: AI agents eating legacy media agencies and services

27:21 Funding philosophy: profitable but still going for a big, signaling Series A

29:13 Bold product moves and the rise of “ChatGPT commerce” (Shopify, Walmart, etc.)

30:05 Hot takes on AI in e-commerce: no AI SDRs, human-led customer success

31:18 Hardest negotiation as a founder: convincing ex-founders to join the mission

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Leyla Kunimoto is the co-founder of Accredited Investor Insights, a platform demystifying private placements, venture funds, and commercial real estate for LPs and high-net-worth investors. She writes for a cross-section of the ecosystem—limited partners, fund managers, RIAs, and wealth advisors—focused on cutting through jargon to what actually drives outcomes.

With thousands of conversations across LPs and GPs and a personal investing journey that started at 19, Leyla distills the messy reality of private markets into practical signal. She launched Accredited Investor Insights in early 2024 to share hard-won lessons and patterns others can use.

She offers insights into information asymmetry, accredited-investor access (and the likelihood of a knowledge test), how alternatives may creep into 401(k)s via target-date funds, the promise and potholes of secondaries and tokenization, the illiquidity tax LPs underestimate, and what the next decade holds as mega-managers court retail capital.

In this episode, she discusses why retail LPs struggle to do “real” diligence, when concentration beats diversification (and when it wrecks you), why secondary liquidity for $50k stakes remains broken, and how better GP reporting separates luck from skill.

In Today’s Episode We Discuss:

00:01 Welcome & what Accredited Investor Insights does

00:31 Leyla’s path: public to private markets

02:18 The “real estate gateway” to alternatives

04:24 Why accreditation limits exist

05:36 The likely future: a knowledge-based accreditation test

06:28 Alternatives inside retirement accounts (via target-date funds)

08:59 Why $50k secondaries rarely clear

10:17 Tokenizing LP interests: promise vs. verification

14:54 Misconceptions to unlearn about private markets

16:57 Illiquidity explained (vs. REITs)

21:03 The retail LP diligence gap

25:42 Concentration vs. diversification: earning the right to concentrate

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

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Visit Our Website: https://www.teamignite.ventures

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