Jan. 17, 2025

281: The Art of Startup Exits | Brian McDonald from Bay Advisory

Brian McDonald is a partner at Bay Advisory, a corporate finance firm helping founders navigate funding, scaling, and exiting their businesses. Brian first joined the show in 2021, and now, four years later, he returns to share updated insights on startup exits, valuations, and the evolving market landscape.

Show Notes
Guest Profile

From the importance of staying true to your business identity to understanding deal structuring and negotiation tactics, Brian breaks down what founders need to know before, during, and after an exit. He also shares his thoughts on current trends, including valuation shifts, the rise of AI-driven businesses, and the significance of knowing when to walk away from a deal.

If you’re a founder planning your next fundraising round or thinking about an exit, this episode is packed with actionable advice and real-world examples that you won’t want to miss.

Key Takeaways:

Stay True to Your Business Identity:
Many founders feel pressured to present their business as a SaaS or AI-driven venture to attract investors, but Brian emphasizes the importance of positioning your business based on what it truly is rather than shaping it to fit investor expectations.
Avoid Venture Capital If You Plan to Keep Your Business Long-Term:
If you’re building a business to own and operate for life, taking on investors expecting a return may not be the right move. Transparency about your vision is crucial in aligning with the right partners.
Consider Alternatives to Full Exits:
Founders don’t have to sell their entire company to achieve financial security. Partial exits or taking some cash off the table while continuing to scale can be viable options.
Valuation Challenges in Today’s Market:
Valuations fluctuate, and generic revenue multiples can be misleading. Founders should focus on comparable deals and be realistic about their company’s value in the current market conditions.
Earnouts and Deal Structuring:
Few exits involve a full cash payout at closing. Earnouts based on future performance are common, and founders should aim for turnover-based earnouts rather than EBITDA-based, as buyers can manipulate EBITDA figures..
Know Your ‘No’ and Be Ready to Walk Away:
Understanding your bottom line in negotiations is critical. If a deal isn’t right, having the confidence to walk away can save founders from making costly mistakes.

Notable Quotes from Brian McDonald:

"If you plan to keep your business for life, avoid taking on investors who expect a return."
"The key question I ask a founder thinking about an exit is ‘What is it that you really want to do?"
" The best founders say to investors ‘This is my business, this is what I'm doing. If this doesn't fit for you as an investor, that’s okay, I’ll bootstrap."

Market Trends and Strategic Insights:

Longer Deal Timelines: Exit processes that once took six months are now stretching to 9-12 months due to market shifts.
AI Bubble: Many businesses are branding themselves as AI-driven when they’re not, which mirrors past trends seen with blockchain startups.
Corporate vs. PE Buyers: Corporates focus on strategic fit, while PE firms prioritize financials and growth potential.
Importance of Data Rooms: Keeping updated documentation can streamline fundraising or an acquisition process when the time comes.

Guest Details: Brian McDonald, Partner at Bay Advisory

Resources & Links:

Listen to Brian’s first appearance on MoneyNeverSleeps in 2021 (episodes 118 and 119, Words of Advice, Parts 1 &2)
Learn more about Bay Advisory and their advisory services for founders
Brian referred to the book A Slight Edge by Jeff Olson in focusing on your niche at the earliest stages