Acquiring Minds Podcast: “Reward for 17-Month Deal: $1.8m of EBITDA”

Host: Will Smith
Guest: Robert Gayden, Owner, BrightStar Care of Greater Waukesha
Date: December 15, 2025

Episode Overview

This episode features Robert Gayden and unpacks his journey of acquiring a home care business in southeast Wisconsin, a process that took 17 months but resulted in purchasing a thriving company with $1.8M in adjusted EBITDA. The discussion spans Robert’s background, the influence of his father’s passing, how he searched for and chose his industry, the specifics of the deal, operational learnings, and his approach to company growth and leadership.

Key Themes & Discussion Points

1. Robert’s Background and Motivations

• Military Family & Upbringing: Robert credits his adaptability and people skills to moving between 11 places as a child due to his parents’ military service. (04:53)
• Banking & Sales Experience: After college, he worked in commercial banking and then in selling fixed-income products. The desire for greater challenge and reward led him to entrepreneurship.
• Business School & Purpose: Attended Carnegie Mellon Tepper School for its ETA (Entrepreneurship Through Acquisition) track, inspired by mentors and professors (08:10).
• Father’s Passing as Catalyst: His father died unexpectedly during Robert’s MBA, making him reconsider his purpose and spurring the desire to build an impactful legacy.

  “People really only talk about how you make them feel… He did a lot of small actions that impacted people’s lives. I started thinking, how can I do that?” — Robert Gayden (10:05)

2. Search Parameters and Industry Selection

• Geographic Constraints: Self-funded, focused on the Chicago-Lake Michigan corridor, including NW Indiana and SE Wisconsin, driven by wife’s medical residency and quality of life goals. (17:38)

• Deal Size Expectations: Initially sought businesses with $300k–$500k SDE, but shifted to aiming for $800k–$1M+ after advice from mentors and self-funded search conferences.

  “The same amount of work that you do in that $300k, it’s going to be the same with $2 million or a million, relatively speaking. So yeah, go for bigger.” — Robert (24:46)

• Narrowing to Home Care: Inspired and mentored by industry veterans, he saw the appeal of low capex, variable costs, and demographic tailwinds by attending the Home Care Association of America conference. (26:58)

  “It’s low capex… Your main cost is variable because it’s tied to your employees—if you lose a client, that revenue is gone, but so is the cost.” — Robert (26:58)

3. The Acquisition Process (A 17-Month Journey)

• Sourcing: Found the business through a broker on BizBuySell, just outside Milwaukee. (38:07)

• Commuting: Robert commutes daily from Chicago—an hour and 20 minutes by Amtrak each way. (41:08)

• Deal Details:

  • Listing price: Just under $7 million.
  • Business had unpredictable revenue over previous years but rebounded strongly (41:32, 46:41).
  • Seller’s margins were unusually high (35–40%) due to active owner-operator husband-wife duo.

• Relationship with Sellers: Integrity and openness on both sides allowed for a smooth deal, even as the purchase price became more favorable with growing EBITDA.

  “They knew my story. I wore that on my sleeve. These transactions are so delicate, and integrity is everything.” — Robert (51:10)

• Deal Structure & Working Capital: No price retrade despite growth, but sellers insisted on taking all working capital out. Robert managed the risk due to process efficiency and cash flow.

  “They didn’t want to leave any working capital… but the business was running so clean… money was going to be coming in.” (64:26)

• Technical Hurdles: Attempted but eventually abandoned a complex F-reorganization for a simpler tax election (336e), which nearly derailed the deal. (55:01, 58:54)

4. Operating and Growing the Business

• Initial Focus: Robert spent the first months hands-on in operations, managing payroll and back office. In hindsight, regrets not investing more time building relationships with field staff and clients sooner.

  “I should have had a more blended approach… I wish I would have had a chance to kind of get out in front of that.” (69:15)

• OPS vs. Sales: Early emphasis on ops efficiency, but realized sales and outward presence drive true growth in home care.

  “The better, bigger, and better lever is good old-fashioned sales.” — Will Smith (72:52)
  “Focusing on sales and presence—being out in the community—pays dividends.” — Robert (73:11)

• Growth Metrics:

  • At closing (2024): Revenue hit $5M; adjusted EBITDA $1.8M+ (61:13, 91:45).
  • Current (late 2025): Revenue on pace for $5.7M+, nearly $2.1M EBITDA (74:19, 91:45).

5. Leadership & Lessons Learned

• Founder Energy: Despite enough EBITDA to hire a manager, Robert chose to be deeply operational—believes this will serve him in future growth and leadership transitions.

  “I actually wanted this… building skill equity… These years will serve me for the rest of my career.” — Robert (80:26, 83:29)

• Team Building & Management:
  • Experiences team turnover as some staff didn’t want to match his new pace.
  • Open about learning to be a more tactful manager.

  “Not yet… I know there’s a level of tactfulness I can get to. I’m laser focused now.” (89:19)

• Franchise Support: BrightStar network provides systems and a supportive network of peer owners. (93:47)

Notable Quotes & Memorable Moments

• On the painful patience of deals:

  “Deals want to die… It takes perseverance and commitment to keep an acquisition transaction alive and get it across the finish line.” — Will Smith (01:54)

• On impact:

  "I just wanted to be in the seat to make those decisions, to position people for success. Whether that’s… really empowering people… everyone has highs and lows… just trying to be there for them." — Robert (15:32)

• On seller relationship and resulting deal:

  “We just kind of got a little lazy… hit our number out of the business… But they blew past projections.” — Robert (46:41) “By the time you close, it’s doing $5M. Is it as good as it sounds? It’s pretty good.” — Will / Robert (61:23–61:37)

• On working in vs. on the business:

  “How do you get stuff done? I was at work – someone comes in, VA calls, and the day is over. He was like, ‘Yeah, that's what it is.’” — Robert recalling mentor advice (76:53, 77:27)

• On management style:

  “I sound like a hard-ass. Yeah, I will share this, the seller’s wife said, ‘The staff is running on all pistons, be mindful of that.’” — Robert (90:33; 91:00)

• On growth and culture:

  “I’m trying to build a world-class home care agency, at least for our area. That starts with every single detail: how we answer the phone, reply to emails, the little stuff.” — Robert (84:07)

Timestamps for Key Segments

• Robert’s Backstory & Motivation: 04:53–11:38
• Father’s Influence & Purpose: 09:58–15:22
• Industry and Deal Search: 17:38–29:45
• Commitment to Home Care Industry: 29:45–37:39
• Deal Sourcing & Early Steps: 38:07–43:10
• Seller Dynamics & Numbers: 43:10–52:36
• Structure, Delays, & Technical Hurdles: 53:11–60:10
• Deal Closing & Favorable Economics: 61:08–64:14
• Operations and Leadership Learnings: 68:41–77:27
• Stepping Out vs. Founder Energy: 78:58–83:18
• Industry Realities & Team Building: 85:41–90:33
• Profitability Today & Franchise Support: 91:35–94:34

In Robert’s Words: The Personal Why

“More than anything… to have an idea and do it in my father's name and being able to acquire with only family and friends… it means a lot to me.” — Robert (94:50)

Takeaways for Acquisition Entrepreneurs

• Relationship with sellers is as critical as numbers in a deal—integrity preserved mutual advantage despite business growth during diligence.
• Go bigger if you can: the work is similar, but the rewards are much greater.
• Operational immersion post-acquisition is invaluable—even when you have the means to hire an operator.
• Home care is people-intensive: success lies as much in motivation and culture as in process.
• Growth comes fastest when the owner is present in the community, not solely focused internally.
• Skill-building as an operator pays dividends far beyond your first company.

End.