How Kerry Boulton of Exit Strategy Group Tripled a Freight Biz to $50M with 63 Staff, Now Guides Owners to Be ‘Exit Ready’ & Spot Their Alan Bond Moment — Secrets on Cash, People & Freedom from 38 Yrs in Business. (Episode 699 - Kerry Boulton)

In this episode of Grow a Small Business host Troy Trewin interviews Kerry Boulton from Exit Strategy Group, who shares her incredible journey of buying a freight business doing $16M and growing it to $50M with the same 63 staff. Kerry reveals how she executed a strategic exit after seven years, then went on to build and sell multiple ventures. Now through The Exit Strategy Group, she mentors owners on being “always exit ready,” balancing business, financial, and personal goals. She discusses the power of systems, the Value Builder tool, and finding your “Alan Bond moment.” Kerry’s story is a masterclass in scaling, cash flow, people, and creating true freedom.

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Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice.

And a snapshot of the final five Grow A Small Business Questions:

1. What do you think is the hardest thing in growing a small business?

According to Kerry Boulton, the hardest thing in growing a small business is managing cash flow. Growth eats up cash faster than most owners expect, and many don’t realize how easily they can run into a squeeze. She says you’ve got to keep a constant eye on cash, plan ahead, and understand that scaling up often means funding gaps you need to prepare for.

2. What's your favorite business book that has helped you the most?

Kerry shares that her favorite business book is “The Seven Habits of Highly Effective People” by Stephen Covey, which she says gave her a rock-solid foundation for both business and life. She also loves “The Great Game of Business” by Jack Stack for teaching how to build financial literacy and an ownership mindset in your team.

3. Are there any great podcasts or online learning resources you'd recommend to help grow a small business?

For podcasts and learning resources, Kerry highly recommends “Built to Sell Radio” by John Warrillow, which dives into making your business more valuable and sellable. She also likes “Business Lunch” with Roland Frasier & Ryan Deiss, plus the Exit Planning Institute’s podcast. And of course, she’s a fan of Troy’s Grow Small Business Podcast, which she appeared on.

4. What tool or resource would you recommend to grow a small business?

When it comes to tools, Kerry swears by the Value Builder System, which helps owners see their business through a buyer’s eyes, score it across key value drivers, and figure out exactly where to improve to maximize value and exit readiness.

5. What advice would you give yourself on day one of starting out in business?

If she could give herself advice on day one of starting out in business, Kerry laughs and says she’d simply tell herself to “buckle up,” because it’s going to be a hell of a ride—full of challenges, personal growth, and ultimately the chance to create freedom and live life on her own terms.

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Quotable quotes from our special Grow A Small Business podcast guest:

Always run your business as if you’ll sell it tomorrow — that’s how you build something truly valuable — Kerry Boulton

Buckle up — because business is the best roller coaster ride you’ll ever take — Kerry Boulton

Cash is the oxygen of your business; ignore it and you’ll suffocate — Kerry Boulton