In this episode of the Directed IRA Podcast, attorney and CEO Mat Sorensen sits down with Ahmed Ahmed , Head of Funds at WeFunder , to discuss how investors can use a self-directed IRA to invest in startups and venture capital —an asset class once limited to Silicon Valley insiders and institutional funds. The conversation explores how WeFunder democratizes early-stage investing through Regulation Crowdfunding (Reg CF) and Regulation D (Reg D) offerings, giving both accredited and non-accredited investors access to vetted startup deals, diversified venture funds, and even pre-IPO companies. Mat and Ahmed explain: How to invest in startups using your self-directed IRA or solo 401(k) The difference between Reg CF and Reg D offerings on WeFunder What the Orange Funds are and how they track Y Combinator companies Real examples of early-stage companies that scaled (e.g. Eight Sleep, Replit) Why diversification is critical in venture investing How to evaluate startup founders and what signals matter most What to expect in terms of risk, timelines, and exit strategies This episode is essential listening for self-directed investors interested in private markets and early-stage innovation—and how to access it within a tax-advantaged retirement account structure. Chapters: 00:00 – Introduction to WeFunder and Startup Investing 01:30 – What Is Reg CF and Who Can Invest 03:16 – Inside the Orange Funds and Y Combinator Strategy 07:40 – Risk, Return, and Realities of Startup Investing 11:50 – Using a Fund Model to Diversify Your Startup Portfolio 19:22 – How to Evaluate Founders, Traction, and Deal Flow 24:27 – Getting Started with Startup Investing Through Your IRA WeFunder Homepage: https://wefunder.com/ Directed IRA Homepage: https://directedira.com/ Directed IRA Explore (Linktree): https://linktr.ee/SelfDirectedIRA Book a Call: https://directedira.com/appointment/ Other : Mat Sorensen: https://matsorensen.com & https://linktr.ee/MatSorensen KKOS: https://kkoslawyers.com Main Street Business https://mainstreetbusiness.com
