Jun 2, 2026 · 31m · we-live-to-build
She Woke Up One Morning and Knew She Had to Buy A $50M Company
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode, entrepreneur Stacy shares how she followed intuition to orchestrate a $50 million software acquisition without formal M&A experience or a college degree. Alongside host Sean Weisbrot, she discusses non-traditional career growth, establishing executive boundaries, conducting due diligence, and prioritizing self-awareness.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 26.3% of the talking time here. How this is scored →
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Stacie rejects Sean's suggestion that she should have aggressively claimed the top executive title, grounding her boundary in a realistic appraisal of her specific strengths.
Hardest push from Sean ▶ 9:15 Why Not Run the CompanySean directly challenges Stacie's decision to accept a reporting role beneath another executive, urging that she should have backed herself to run the entire enterprise.
Biggest teaching moment ▶ 14:55 Real M&A Due DiligenceStacie clarifies the mechanics of institutional broker transactions, pointing out that legitimate deals grant open due diligence rather than charging consumer-style access fees.
Sean holds their own ▶ 13:15 Analyzing Recurring Revenue RiskSean demonstrates his commercial acumen by contrasting high-ticket consulting models with low-ticket recurring SaaS vulnerable to external platform algorithm shifts.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| Leading a $50M Acquisition and Overcoming Executive Disrespect | 2 | 3 | 2 | 1 | Stacie recounts orchestrating a $50M acquisition and resisting an elitist CEO who excluded her from the org chart. Sean facilitates with exploratory and clarifying questions while validating her appraisal of the CEO's poor leadership. | |
| Sponsor Break: Network Before You Need It | 3 | 3 | 2 | 4 | Sean pushes Stacie on why she settled for a subordinate role instead of aggressively demanding the CEO seat. Stacie counters by explaining her self-awareness regarding software engineering versus implementation services. | |
| Sean's Acquisition Attempt and Direct Deal Due Diligence | 4 | 4 | 1 | 1 | Sean describes his own hesitation acquiring a $4M business when faced with online listing platform paywalls. Stacie explains that standard broker-led M&A deals provide direct due diligence access to serious buyers without micro-fees. | |
| From Bartending to Rolling Out IBM PCs Across HHS | 3 | 2 | 1 | 1 | Stacie shares her unconventional transition from hospitality to IT deployment at HHS. Sean compliments her rare ability to execute effectively rather than merely being a passive beneficiary of mentorship. | |
| Analytical Systems Thinking, Fast Processing, and Listening Skills | 4 | 2 | 1 | 1 | Sean candidly reflects on how his ADHD and rapid information processing have historically created communication friction in personal relationships. Stacie concurs on analytical framing while reminding him that active listening is a deliberate skill. | |
| Peace of Mind, Self-Awareness, and Life Advice | 3 | 2 | 1 | 1 | Stacie discusses prioritizing peace of mind and self-awareness over conventional academic credentials. Sean connects with her perspective by sharing his choice to abandon psychology graduate school to teach in China. |