From Rock Bottom to $100M ARR: Josh Mastel on Resilience and Exit
Most founders think the goal is to build something big enough to sell.
But what happens when the business still works… and you don’t?
In this episode of Your NEXT, Jerome Myers sits down with Josh Mastel to talk about entrepreneurship, resilience, alignment, and what it means to leave a business before it drains the life out of you.
Josh shares the story of cashing out his 401(k), savings, and every available dollar to bet on himself, getting fired early in his career, losing his brother at 18, building a sales consulting company he eventually fell out of love with, and then joining his wife’s company to help scale it into a $100M ARR technology services business.
This is not just a conversation about exit.
It is a conversation about knowing when something is no longer serving you, having the courage to walk away, and building a life around the things that actually matter.
If you are a founder, operator, or leader trying to figure out whether your business is working for you or you are working for it, this episode will hit.
In this episode, we cover
Why Josh says Easy Street is dangerous
The hard decision to cash out his 401(k) and bet on himself
What getting fired early in life taught him about confidence and humility
How losing his brother shaped his resilience
Why he exited a business that was still functioning
The difference between building for money and building in alignment
How he and his wife built a company to $100M ARR
Why priorities matter more than income
The hidden trap of becoming a slave to your own business
What founders need to think about before they become work-optional
Key Takeaways
Hard things do not make life worse. They often make life meaningful.
Alignment matters more than momentum.
Money is a tool, not a compass.
You cannot be great at everything. You have to decide what matters most.
The business should work for you, not the other way around.
Memorable Quotes
“Do what is hard and your life will be easy. Do what is easy and your life will be hard.”
“You can take my business from me. You can empty my bank accounts. But you can’t take what I’ve learned.”
“You can’t be victim to the thing you built.”
“Sit down with a pen and paper and figure out what’s really most important to you in life.”
Chapters
00:00 Intro
05:18 Josh’s morning with his brutally honest daughter
06:19 Building a personal brand on LinkedIn
07:42 A small exit and what it really meant
09:55 The truth: every founder exits one way or another
12:34 Walking away from comfort and cashing out everything
15:47 Getting fired and the first real failure
17:33 Moving out at 16 and losing his brother at 18
18:56 Resilience, hard things, and self-discipline
19:47 4x4x48, 75 Hard, and challenge as training
24:32 What he was thinking when he cashed out his 401(k)
25:40 Why skills matter more than what’s in your account
27:51 How he joined his wife’s business and helped scale it
29:02 What the company actually does
32:27 The biggest lesson from the exit
34:37 Hard things vs happy life
36:26 Fatherhood, priorities, and real alignment
39:23 What changes when money is no longer the decision-maker
45:18 The 70-year game and building a life your kids want to return to
49:18 Why he left a business that no longer felt aligned
52:37 The vision ahead and what comes after this chapter
55:58 Final takeaway: get your priorities straight
57:51 Jerome explains the real mission behind Exit to Excellence
59:52 Why founders should not wait until after the exit to think about what’s next
About Josh Mastel
Josh Mastel is an entrepreneur, sales leader, and operator based in Atlanta. After building and exiting a sales consulting business, he joined his wife’s company, helping scale it into a $100M ARR technology services firm. He is passionate about leadership, growth, resilience, and helping younger professionals think bigger about what their lives and businesses can become.
About Jerome Myers
Jerome Myers is the founder of Exit to Excellence and a leading voice on the emotional and psychological side of business exits. His work helps founders prepare not just for the transaction, but for the transition that comes after it.
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