What You Need to Know Before Investing in Startups | Jaclyn Johnson

Private investing is having a moment - but should you actually be investing in startups? Serial entrepreneur and investor Jaclyn Johnson joins Mary Holland to breakdown what you need to know before putting your money into a private company: who can invest, how much risk you should actually take, why your money could be tied up for years, and what really has to happen before an investment pays off. And Jaclyn knows risk from both sides of the table. She built Create & Cultivate from scratch, sold the company for $22 million, and later made the unexpected decision to buy it back. She gets candid about: what a $22 million exit actually means for a founder what she did when the money hit her account how she thinks about knowing when “enough” is enough why emotion isn't always the enemy when making big business decisions. Plus, Jaclyn shares what she’s learned investing in companies like Away, Chillhouse, and Crown Affair—and what she looks for before writing a check today. Whether you're curious about angel investing, building a company of your own, or just trying to understand how wealthy people think about risk, this episode will help you ask a better question: What kind of risk actually makes sense for me? Chapters: 00:00 - Welcome Jaclyn Johnson 04:06 - How to Start Angel Investing with Small Check Sizes 07:56 - The Value of Building Social Capital 09:21 - Cap Table Curation & Modern Investor Strategy 11:00 - Portfolio Diversification & Tax Incentives (Roth IRA) 15:08 - Three Essential Questions for Founders Before Investing 18:59 - Overcoming a Scarcity Mindset as an Entrepreneur 19:33 - The Story Behind Selling Create & Cultivate 28:44 - Financial Advisors & Wealth Management Strategy 31:15 - Buying Back Create & Cultivate 41:00 - How AI & Modern Tech Tools are Lowering Startup Costs 42:15 - The Future of Early-Stage VC and Angel Investing 48:08 - Notable Personal Investments & Shifting Portfolio Focus 50:24 - Hobbies, Travel, & Closing Advice Produced by Dear Media. About Growing Interest: On ‘Growing Interest’, join Mary Holland Nader as she explores her curiosity and passion for how psychology, habits, and real-life behaviors shape how we earn and spend. Through thoughtful conversations with experts, professionals, and her friends - plus behind-the-scenes insights from her own life as an investment manager, founder, and reality personality - each episode will deliver practical, doable shifts that make financial wellness feel less overwhelming and more human. New Episodes are out every Tuesday. Keep Growing Your Interest 🌱 Have a money question, topic, or guest you want us to dig into? Email us at growinginterestpodcast@gmail.com Watch + Follow Growing Interest YouTube: @GrowingInterest Instagram: @GrowingInterestWithMaryHolland TikTok: @GrowingInterestPodcast Keep Up With Mary Holland Instagram: @MaryHolland TikTok: @Mae LinkedIn: @MaryHolland A Little More Interest 💸 Sign up for the Mary & Pip finance app waitlist Get the free Mary & Pip newsletter Visit MaryandPip.com DISCLOSURE: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. All investing involves risk, including loss of principal. Guests and the host may own securities discussed on this show, and nothing said here is a recommendation to buy or sell any security. Always do your own research and consult a licensed financial advisor before making financial decisions. This podcast is not produced, reviewed, or endorsed by Mary & Pip Investments LLC, a registered investment advisor, nor its affiliates. Nothing said here reflects the views, advice, or services of that firm.