Jon Staenberg was an early employee of Microsoft, one of its first 2,500 hires, before becoming a General Partner managing over $325 million across three venture funds.

He's invested in 400+ companies including Facebook, Splunk, Avalara, Docusign, and Seagate, plus made over 250 personal angel investments along the way.

Today he runs Agate Hound Fund, the first-ever fund of funds for search funds — an asset class he says has delivered 35% net annual returns over the past 40 years.

In this episode, Jon shares stories and lessons from the early days of Microsoft working with Bill Gates, why heroes are crucial for success, and what he learned from Warren Buffett.

He also breaks down how to put yourself in a position to get lucky, and why he believes search funds are the next big thing in investing.

Paul Swegle is a former SEC and DOJ attorney turned startup lawyer who has completed more than $15 billion in financings and M&A deals.

He's helped build and sell four companies to publicly traded acquirors like Capital One, Abbott Laboratories, ING, and Nortek, taken a startup public at a $522 million market cap, and was part of a $9.5 billion exit. He's also a bestselling author on startup law and fundraising.

In this episode, Paul shares deal-making lessons from his $15 billion career, why founders should understand the laws and regulations that govern their business, and the story of a client hit with fines and regulatory oversight over an ad campaign.

He also shares real stories of founders getting scammed by partners and employees — and how to spot and avoid it before it happens to you.

Mark Benak was the CEO of Asset Performance Technologies (APT) which was acquired by Uptake for 8 figures. He now angel invests in tech startups.

In this episode, we discuss his regrets from his exits and how he decides to invest in companies as an angel investor.

Len Lehmann is a 30-year Silicon Valley entrepreneur and investor who co-founded three venture-backed companies, including Global Village Communication, which he grew to over $100 million in revenue before it listed on NASDAQ.

He's also an angel investor with Sand Hill Angels, a Silicon Valley investment group of accomplished tech executives. In this episode, Len shares the lessons from landing funding from Sequoia Capital and the questions all investors ask themselves when deciding who to fund.

Martin Tobias is a serial entrepreneur who's founded three venture-backed companies (with two successful IPOs), raised over $500 million for his own startups, and personally invested in over 250 companies as an angel — including 4 unicorns whose portfolio companies went on to secure more than $2.5 billion in follow-on financing.

His own journey includes founding Loudeye Technologies (later sold to Nokia) and leading Imperium Renewables, which built the largest biodiesel refinery in the US. In this episode, Martin shares how he lost $500M after building a $2 billion public company, how he became one of the best venture investors in the world with an 8% unicorn hit rate, how he raised $250M as a complete outsider for Imperium, and the two things all successful founders have in common.

Chris Haroun was an early investor in Facebook and Palantir, pre-IPO, and has raised and managed over $1 billion across his hedge fund and venture capital career — including stints at Goldman Sachs, Citadel, and Accenture.

He's since built Haroun Education Ventures into a platform with over 2 million students across 196 countries, and authored "101 Crucial Lessons They Don't Teach You in Business School," which Business Insider named the most popular book of 2016 and Forbes called a must-read for entrepreneurs.

In this episode, Chris shares stories on overcoming a fear of public speaking (learned in jail, before giving a TED Talk), the one trait every billionaire he's met shares, meeting Doug Leone of Sequoia, how a Persian rug merchant accidentally invested in PayPal, body language lessons from FBI/CIA veterans, and the networking trick that can land any client or job in the world.

Matt Wilson is an angel investor, venture capitalist, exited entrepreneur, and former sales executive at Nestlé and Coca-Cola. Some of his most famous investments include Lyft ($24 billion IPO) and Pinterest ($12 billion IPO), made during his early years learning the venture game.

Today he's Founder and Managing Director of Allied Venture Partners, Western Canada's largest angel syndicate, which has deployed over $6 million into startups, with Matt personally investing in over 100 early-stage companies.

In this episode, Matt shares stories from angel investing, including his own path from founder to investor, and the lessons that shape how he evaluates deals today.

Frederic Gray is a VC at Techstars — an accelerator with a portfolio now worth more than $300 billion — and the exited founder of Packfed.

Across Techstars, Bread & Butter Ventures, and his own angel investments, he's backed roughly 175 companies, including unicorns like PrizePicks (recently acquired in a $1.5 billion deal) and Felix Pago, alongside notable exits like Avail Finance's $120M sale.

In this episode, Fred shares the story of passing on a startup that went on to become a $4 billion unicorn, why he decided to back PrizePicks early, fundraising lessons from being a founder turned VC, and tips for getting into Techstars.

David Mandel is a "Super Angel" with more than 500 early-stage tech investments to his name, and Managing Partner of Emerging Ventures, a firm backing pre-seed and seed-stage B2B startups.

Before turning to tech investing in 2014, he built, operated, and exited four successful businesses in the insurance and finance industries over a 28-year career, applying that same systems-driven, risk-modeling mindset to how he evaluates startups today.

In this episode, we go inside David's investing brain — his first few investments, the deal that excited him most, how three college students who barely spoke English closed $2 million in contracts with the Navy and a major oil company, and the biggest mistakes and wins from 500+ bets later.

Phil Fraser launched William Hill's first-ever online casino in 2000 before founding WhichBingo, which grew to become the UK's largest bingo review platform — built entirely from 0 to an 8-figure exit with zero outside funding. WhichBingo was later acquired by Gambling.com Group, a major public player in online gambling.

Phil is now an angel investor and mentor to founders navigating the same bootstrapped path he took. In this episode, Phil shares stories and lessons from building, scaling, and exiting WhichBingo — entirely on his own terms.