Growing Interest with Mary Holland Nader

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

September 8, 2026

AI Summary

5 min read

In 2012, Jaclyn Johnson wrote a $10,000 check into a company called Away. That investment eventually returned $1.2 million. It is the kind of story that makes angel investing look like a lottery ticket, but Johnson, a serial entrepreneur who has built, sold, and bought back Create & Cultivate, is careful to explain that this outcome is the exception, not the rule. In a conversation with Mary Holland Nader on Growing Interest, she walks through what private investing actually requires, how to think about risk, and what she learned from being on both sides of the cap table.

What Private Investing Actually Is

Private investing means buying ownership shares in companies that are not listed on public exchanges. Unlike the stock market, where anyone can buy and sell freely, private markets are exclusive. The company itself decides who can invest, and investors must meet SEC rules for accredited investor status: an individual must earn $200,000 per year (or $300,000 as a married couple) or have over $1 million in liquid assets excluding a primary residence. The purpose of these rules is not gatekeeping for its own sake, Johnson explains, but investor protection. Private investments are illiquid and high-risk. You cannot wake up the next day and ask for your money back. Most startups fail within the first two years, and investors should expect to hold for five to ten years befo

Continue reading the full summary in the app — free to try.

Read Full Summary →

Free • No credit card required

Listen to Audio Summary Open in App

Never miss an episode of Growing Interest with Mary Holland Nader

Get every new episode summarized in your inbox — free, ~5 minutes to read.

No spam. Unsubscribe anytime.

What you'll learn

1 (01:54) **Private Investing Defined** - Jaclyn explains what private investing is and how it differs from public markets
2 (03:11) **Accredited Investor Requirements** - The SEC rules that determine who qualifies to invest in private companies
3 (04:04) **Where Angel Investing Fits in Your Financial Life** - Jaclyn explains the pecking order for allocating money to private investments
4 (05:17) **The Reality of Unicorn Returns** - Jaclyn shares her $10K check that returned $1.2M from Away and explains the odds
5 (07:59) **Beyond Financial Returns: Social Capital** - Why angel investing offers more than just money
6 (09:27) **The Shift to Strategic Cap Tables** - How founders now curate investors for more than just money
7 (11:55) **Roth IRA Angel Investing and the Angel Act** - Two emerging opportunities that could change private investing

+ Full timestamped outline available in the app

Show Notes

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?

Keep Up With Mary Holland

Instagram: ⁠@MaryHollandNader⁠

TikTok: ⁠@MaryHollandNader⁠

LinkedIn: ⁠@MaryHolland⁠

A Little More Interest 💸

Produced by ⁠Dear Media⁠

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.

Learn more about your ad choices. Visit megaphone.fm/adchoices