Business Unchained
Calling all business warriors who feel chained to their business! Do you run your business or does your business run you? You've poured your blood, sweat and tears into it and it is time to set yourself free. I'm Bobby Mascia – owner of a wealth management firm, family office, manufacturing business, 18 store Dunkin Franchise, and de facto business coach. My goal? To liberate your business— whether it be operationally, prep for a sale, a legacy handover, or self-management. The roadmap to this freedom is something we will uncover together in Business Unchained." Join me as I learn about fellow entrepreneurs, dissecting their past, present, and future.
Business Unchained
10 Years. 5x Growth. One Lesson: Jordan Kaufman on a Powerful Business Partnership
About Jordan Kaufman
Jordan Kaufman is the Chief Investment Officer, Adviser, and Partner at Green Ridge Wealth Planning, where he works alongside host Bobby Mascia to help entrepreneurs and business owners build wealth, de-risk their personal finances, and become exit-ready long before they want to sell. He grew up around family-run businesses, so he doesn’t just “know the theory” of entrepreneurship; he’s lived the messy parts: delegation, scaling teams, navigating volatility, and staying sane when your company wants to eat your calendar alive.
Reference Links:
- Grab a copy of Bobby Mascia’s book Unchained: The Raw Truth About Entrepreneurship, Family Business, and Life Balance: https://a.co/d/dSwUruD
- Green Ridge Wealth Planning
- BobbyMascia.com
- Instagram - Bobby Mascia
- Instagram - Business Unchained
Jordan Kaufman
Episode Highlights
Green Ridge Wealth Planning just hit 10 years in business, and Bobby Mascia brings Jordan Kaufman on to break down the real story behind their 5x growth: not some secret hack, but the power of delegation, role clarity, and evolving before you’re forced to. If you’re a founder trying to scale without burning out, this episode is basically a field guide for turning “wearing 10 hats” into “owning 1 role and actually winning at it.”
“We got to kind of compartmentalize our own things that we focused on, and I think that was incredibly beneficial…” - Jordan (02:29)
The conversation then shifts into exit planning for entrepreneurs: why waiting until you’re “ready to sell” is the worst possible time to start, how strategic buyers find value you’re not even seeing, and why selling creates real fatigue (and distractions) that can tank operations if you’re not prepared.
“Don’t be afraid to talk to professionals to hear about ways… they might be able to amplify or better your business.” - Jordan (55:07)
Jordan also breaks down investment philosophy for business owners, especially around liquidity, risk, and behavior (because “staying invested” is the real boss fight). The thread through it all is simple: stop aiming for survival and start engineering “thriving.”
In This Episode
- 00:00 — Introduction
- 00:57 — 10 years in business: Green Ridge’s story + the 5x growth partnership
- 02:29 — Delegation that actually scales: “give away the hats” and focus harder
- 06:12 — Different kinds of entrepreneurs: age, life season, risk appetite, and bandwidth
- 09:06 — Founder habits at scale: why being “designated hitter everywhere” breaks the team
- 11:26 — Freedom of time vs control of time: building systems to stay in your zone
- 18:33 — Exit-ready vs last-minute exits: runway, blind spots, and mindset diagnostics
- 20:03 — “Your business is sellable”: strategic buyers, hidden assets, and value beyond cash flow
- 28:11 — Be ready early: market timing, stamina, and going for the best price (not just “good enough”)
- 47:24 — Survival vs thrive: building a business that runs “cool as a cucumber”
- 59:42 — AI and productivity: Why 2026 is the year to experiment
- 01:07:46 — Investing for business owners: liquidity, risk, and cash-flow replication after the exit
- 01:22:27 — The 1,000 exit-