Acquiring Minds: "The Late 40s Pivot Into Business Buying"

Host: Will Smith
Guest: Jerem Wren, Owner of Van Life Outfitters
Release Date: January 29, 2026

Episode Overview

This episode of Acquiring Minds features Jerem Wren, a successful corporate executive who, in his late 40s, made the bold transition to entrepreneurship through acquisition (ETA). Jerem shares his journey from feeling "trapped" in a lucrative but unfulfilling corporate career to buying an e-commerce business—Van Life Outfitters—that celebrates the very freedom he sought. The conversation delves into the unique challenges and perspectives of pursuing ETA later in life, practical deal mechanics, risk assessment, lessons learned, and actionable advice for mid-career and late-career professionals considering a similar leap.

Key Discussion Points & Insights

1. Jerem's Corporate Background and the "Itch" for Change

• Working-Class Roots & Climbing the Ladder:
  Jerem details a background that drove him to carve out security and success through a "classic American" approach: school, big company, increasing responsibility — and ultimately, a lucrative career.
  "My grandpa grew up on an Indian reservation, my dad was the first to go to college, we moved a ton and never had any money... I wanted to go to good school, get a good job, work for a big company, work my way up and make it." [04:00]

• Recognizing the Tradeoffs:
  After 20 years in brand management, Jerem realized he was “renting himself to a corporation.” The lack of control over time and location became unshakeable.
  "It really boiled down to... I'm renting myself to a corporation. And once that phrase hit me 10 years ago... I wanted to find a way to own my own time." [05:05]

• Corporate Constraints Crystallized by Forced Relocation:
  Company forced a relocation to Texas, which was the breaking point.
  "I moved to Texas, but I didn’t really want to. Not having control over where I live was the crystallization—I need a way to be in charge of my life." [07:44]

2. Discovery of Entrepreneurship Through Acquisition (ETA)

• The Epiphany:
  Listening to a friend who had been a CEO & then bought a business through ETA.
  "I was mesmerized. I had never heard of a regular person buying a business… He put down $100,000 and bought a million dollar business." [11:14]

• Overcoming Misconceptions:
  Believed ETA was only for "rich people."
  "I had never heard of it. Rich people buy businesses. I don’t come from money... He did the SBA style, self-funded search, the regular thing." [12:11]

• Jerem’s Age: Starting Considerations at 38, Discovery at 47
  "I was probably 38 when I started thinking I needed a different path. It wasn’t until I was 47 that I learned about ETA." [09:31]

3. Risk Assessment: Later-Stage ETA Considerations

• Why ETA Felt "Less Risky" Than Corporate:
  Fears about sudden job loss and loss of control outweighed business risk.
  "Taking control of my own career, my own life, felt less risky to me." [14:39]

• Financials & Family Security:
  Walked away from a “mid six-figure salary,” but had cash reserves for 12–24 months.
  "I could live without working for 12 to 24 months... and was confident... I could make it work in that time." [16:13]

• The Worst-Case Scenario:
  "If this goes all the way to bankruptcy, then I'm wiped out… starting over in my 50s... it's worse than for a 30-year-old." [18:31]

• Corporate Risk Paradox:
  Higher up the corporate ladder meant harder to find equivalent roles if laid off.
  "It’s actually harder for you to go and get another job… there’s just fewer jobs that are well suited to you versus the 30-year-old.” [19:31]

4. Search Process & Deal Criteria

• Deliberate, Phased Approach:
  Researched for 6 months, notified employer, then planned for transition out.
  "I’d heard the main thing I was worried about was quitting... and then not finding a business for 18 months. So I decided to get my practice while working." [22:33]

• Search Parameters:

  • Digital/Online businesses: $150K+ SDE
  • In-person businesses: $500K+ SDE
    "I was focusing on online because I could maybe do it part-time... but for a local business, I'd have to quit immediately—so needed to be bigger." [24:00]

• Balance Sheet & Self-Reliance:
  ~$350K in cash, most net worth in 401k, preferred not to use outside investors.
  "I really wanted independence. I was willing to take a sizable pay cut to do that... I didn't want investors because I wanted to be independent." [29:38]

5. The Deal: Buying Van Life Outfitters

About the Business:

• Niche: E-commerce store for van conversion parts & accessories, serving DIY “van life” community.
• Origin Story: Started as a blog, built trust and education before commerce [47:33].
• Financials: SDE was $1M+, dropped to ~$750K after financial revision [56:37].
• Structure: Inventory-heavy (six figures), 10 employees, recent rapid growth (2016 blog, e-com since 2020).

Why It Was Appealing:

• Personal Fit:
  "Ultimate freedom... get in a van and go, decide tomorrow where you want to stay that night. The correlation between the freedom I was looking for and that this company is giving their customers just lit me up." [31:14]

• Industry Upside:
  Small but growing sliver of the massive RV market; European model hints at larger TAM.
  "It's such a small piece of an enormous pie... Europe is way ahead of us." [34:22]

Risks & Challenges:

• Youth of Business (Founded 2020 as a store):
  "Biggest risk was its lack of longevity—only four years old." [35:46]
• E-commerce Lending Aversion:
  "Banks that will not loan for E-com, so I don’t see it as a weakness, but the industry does." [43:29]
• Low Gross Margins (~30%), Net Margins (10–15%).
• Financial Diligence Issues:
  Original SDE overstated, 20% drop in revised financials [56:37].
  "They had inaccurate COGS calculation... it was a bootstrapped business by DIY-ers who were new at financials." [55:46]

Differentiation vs. Amazon:

• Content and Trusted Expertise:
  "DIYers need help... lack of content and education exists still today. One moat we have is four years of content and trust built up strictly through education." [47:33]
• REI and Chewy Analogy:
  "There are reasons to go to Chewy and REI, and I think we can continue to build that." [50:46]

6. Deal Mechanics: Twists, Negotiations, and Problem-Solving

• Initial LOI and Sudden Financial Restatement:
  SDE drops by 20%; scares off buyers and banks.
  "One of the issues that came up is I put in an LOI, and two weeks later... 'we need to redo the financials.'” [52:56]

• Jerem’s Steadiness:
  "Every deal I find is going to want to die. I can't run away because the next deal will also want to die." [54:02]

• Bank Rejections:

  1. E-commerce stigma
  2. Revised, uncertain financials
  3. SBA loan complications: cash-vs-accrual accounting; not enough tax history
     "Most banks were saying no... E Comm, change in financials, and taxes compliance." [55:34]

• Broker’s Advice and Confidence:
  A respected broker warned Jerem to run; he pressed on, reliant on “deals want to die” wisdom.
  "Loan broker... wrote me long emails: this is dangerous; don't do it." [62:19]

• LOI Adjustment:
  Switched to a multiple (mid-3s) of final QofE SDE; successfully negotiated a partial acquisition (70%), sellers kept equity.
  "I tied the valuation to a future QofE assessment... We agreed to the multiple and that’s how we moved forward." [58:42]

• Quality of Earnings Dilemma:
  Costs ranged from $45K (full scope) to $10K (numbers verification); chose the latter due to deal risk & his confidence analyzing numbers.
  "If you're comfortable with a P&L... try a lower cost Q of E—just verify the numbers." [66:00]

7. Post-Closing: Transition, Early Lessons & Reflections

• Role and Transition:
  Sellers became minority partners, transitioned to advisory/BOD role.
  "We agreed they'd leave day-to-day management and essentially become a board.” [76:23]

• Team Building:
  Promoted managers, hired van life experts, created organizational structure [78:08].

• Reality Checks:
  Balance between working “on” vs. “in” the business harder than expected.
  Store platform risk underappreciated—store crashed, emergency migration to Shopify.
  "Do a risk assessment on the business. If I'd done that, our store would have been at the very top." [81:07]

• Size Matters for Owner-Led ETA:
  "I'd buy the biggest business possible... risk is enormous if you buy small." [86:21]

• Personal Pay Cut & Choice:
  Paying himself roughly half of old comp; lifestyle contraction mostly in "extras" (e.g. vacations).
  "Day to day life is covered. I won't be going on vacations to Italy for a while nor moving there." [92:33]

• Core Benefits Already Delivered:
  "I'm in charge of my time... I work on things I think I should be working on... and I can live wherever I want already." [79:40]

8. Advice for Later-Stage Searchers & Closing Thoughts

• Midlife ETA is Different, Not Impossible:
  Unique risks, but also unique levers—more capital, experience, and clarity of purpose.

• On Getting Started:
  "I read a book before starting the search and there was a quote: 'Don't get ready, get started.' That really drove me to act differently... You'll probably never be ready, so don't focus on getting ready. Focus on getting started." [93:03]

Notable Quotes & Memorable Moments

• “I was renting myself to a corporation. And once that phrase hit me… I wanted to find a way to own my own time.” — Jerem [05:05]
• “I had never heard of a regular person… buying a business.” — Jerem [11:14]
• “Taking control of my own career, my own life felt less risky to me.” — Jerem [14:39]
• “Every deal I find is going to want to die. I can't run away because the next deal will also want to die.” — Jerem [54:02]
• “Do a risk assessment on the business. If I'd done that, our store would have been at the very top [of the risk list].” — Jerem [81:07]
• “Don’t get ready, get started… You’ll probably never be ready.” — Jerem [93:03]
• “I would buy the biggest business possible… buying a small business leaves you open to the problems of entrepreneurship.” — Jerem [86:21]

Timestamps for Key Segments

• [04:00] Jerem’s career background and realization about corporate life
• [09:31] Age, family context, the timing of pivot and ETA discovery
• [14:39] Risk/reward considerations for mid-life corporate escape
• [22:33] Designing the search process; balancing work and prep
• [24:00] Search criteria for digital vs. local businesses
• [31:14] Discovery and acquisition of Van Life Outfitters
• [35:46] Risks: youth of business and COVID-era (over)performance
• [43:29] Differentiation from Amazon; the power of community and content
• [52:56] Deal drama: restated earnings, bank refusals, emotional management
• [66:00] QofE decisions — choosing a $10K verification over $45K “consulting deck”
• [76:23] Transition, structure, working on vs. in the business
• [81:07] Big lesson: not prioritizing platform risk nearly enough
• [86:21] Size as risk mitigator—why small businesses are often riskier
• [93:03] Final advice: don’t wait, get started

Final Thoughts

This episode offers a candid deep dive into the realities, anxieties, and practicalities of buying a business in mid-to-late career. Jerem Wren’s example shows:

• The unique leverage and risks that come with experience and age
• The importance of clarity on personal goals (freedom, control, location independence)
• Why most deals “want to die” and how persistence, flexibility, and emotional stability are differentiators
• That buying a business—even later in life—is not only possible, but can be liberating

Essential advice for aspiring ETA entrepreneurs at any age:
"Don't get ready, get started… You'll probably never be ready, so focus on getting started." [93:03]

Resources

• Van Life Outfitters: [Link in show notes]
• Jerem Wren's LinkedIn: [Link in show notes]
• Related episode: Harley Sitner / Peace Vans (vanlife business in Seattle)

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