Surviving the Side Hustle

Any monkey can do multifamily real estate. That is what Gino Barbaro told me, and he would know. Gino went from a restaurant kitchen to co-founding Jake and Gino, a multifamily education company with over $100 million in assets under management, and he has coached thousands of investors along the way. His point is that most people skip straight to strategy, and strategy without the right mindset a...

For 20 years Gino Barbaro was the pizza guy. Then he started a side hustle in multifamily real estate that grew into over 1,900 units and $450 million in assets under management. Gino is a certified money coach, the author of Happy Money, Happy Family, Happy Legacy, and the founder of Barbaro 360, a family coaching brand built around legacy and money. He walks Rob through the phone call that chang...

If you try to do everything, you will do nothing well. That line came from Jordan Meyer, the founder of Addie Health, and it stopped me when he said it. Jordan is building a skincare brand formulated specifically for people on GLP-1 medications like Ozempic and Wegovy, and before that he was the CEO who led Obagi through a hardcore turnaround: an SEC investigation, the threat of being delisted, an...

Most of the decisions keeping you stuck do not matter nearly as much as you think. Jordan Meyer is the founder of Addie Health, an Austin based skincare brand built for the 30 million Americans on GLP-1 medications, and the former president of Obagi, where he led a hardcore turnaround through an SEC investigation, a near delisting, and 80 to 90 hour weeks. He walks Rob through what that pressure t...

Picture a room nobody wants to be in: grieving siblings who have not spoken in years, and a funeral director who has about three minutes to earn their trust. That was Jay Jacobson's classroom for 45 years. Jay is the founder of Jacobson Professional Staffing and the guy behind Jay's Cookies, and he now teaches the skills he built in those rooms to the next generation of leaders. In this Friday rec...

You have about three minutes to earn someone's trust, and in funeral service that is all you ever get. Jay Jacobson spent 45 years in funeral service, founded Jacobson Professional Staffing, runs the gourmet cookie company Jay's Cookies, and wrote Lead by Legendary Example. He walks Rob through what a lifetime of sitting with families on their hardest days taught him about leadership, trust, and p...

"You have two choices when life knocks you flat. You can be a victim of your circumstances or you can be a victor." Anthony Guastella lived that choice for six years with Lyme disease, through joint pain, thyroid issues, and doctors telling him this was just his life now. He said no, went hunting for answers, and made himself a promise: when he got to the other side, he would do the same for other...

Six years of Lyme disease, joint pain, thyroid issues and fibromyalgia left Anthony Guastella with two choices: be a victim or be a victor. He chose victor, and the number one tool he used to find answers was podcasting. Today Anthony is the founder of Anthony Guastella Wellness, a certified health coach, speaker, podcaster and the writer of more than 350 articles, and he walks Rob through how tak...

"I hold a lot of trauma in my throat." That is how Shakti Sharma described her starting point: a shy kid who wanted to stay in the corner and not be seen. Today she is a serial entrepreneur, a manifestation coach, and the founder of the Feminine Wealth Movement, where she helps women entrepreneurs, coaches, healers, and service providers turn a passion into a 100K offer sold directly to organizati...

Nobody showed up to the opening of Shakti Sharma's first yoga studio. One person walked in a day or two later. Shakti spent 12 years in financial services, management consulting, and investment banking, then built an intuition practice on the side before making the leap. From that empty room she grew to consistent $10,000 months, expanded next door, bought a second studio, and watched the pandemic...

What if the thing keeping you stuck is not a lack of hustle but a lack of permission? This week I am unpacking my conversation with Jeremy Shapiro, founder of Your Business Growth Playbook and a serial entrepreneur who has spent three decades in the trenches with seven, eight, and nine figure founders who hit a plateau and cannot figure out why what got them here will not get them there. Jeremy ha...

Can you build something real without it costing you everything else? Jeremy Shapiro has spent 30 years answering yes. A serial entrepreneur and the author of Your Business Growth Playbook, Jeremy has built companies that let him live abroad, unplug for three months at a time when each of his kids was born, and travel entire summers without the whole thing falling apart. He walks Rob through exactl...

Passion done with consistency and integrity over a long enough timeline becomes a legacy. That one line from Erica Christ has been sitting with me all week. Erica is a registered dietitian, a diabetes educator, and a classically trained Pilates instructor who has spent twenty years building FMR Wellness in Greenwich, Connecticut, one private session, one client, one word of mouth referral at a tim...

For 20 years Erica Christ has built FMR Wellness the old fashioned way, with no roadmap and no mentor handing her the playbook, just a commitment to classical Pilates while the rest of the industry chased the next trend. Erica is a registered dietitian, a diabetes educator, and a classically trained Pilates instructor, and she walks Rob through what it takes to build a business around a real mind-...

Jordan Reeves is not a real person. He is a composite of 53 real business owners I sat down with over one summer of research conversations, and there is a very good chance he is you. Coaches, creatives, real estate operators, wellness practitioners, all of them kept describing the same wall, the same frustration, and almost word for word the same breakthrough. The biggest shift was never a new fun...

Jordan Reeves does not technically exist. He is a composite of 53 real business owners Rob sat down with over one summer of research conversations, rolled into a single story. And there is a very good chance that this person is you. Coaches, consultants, creatives, real estate operators, service providers of every kind kept telling Rob the same story, the same wall, and the same frustration, so he...

A pivot is not a failure. Sometimes it is the most strategic move you can make. That is what my buddy John Mendez proved, and he is not just any guest. John was the very first interview I ever recorded for Surviving the Side Hustle back in 2023, he came back for our 100th episode, and now he is here for a third time. The world still saw him as the AI guy while his income was taking a nosedive, his...

The results you are looking for are not in the breadth of your knowledge. They are in the depth of your execution. John Mendez said that about halfway through this conversation and it reframes almost everything people reach for when business gets hard. John was the very first guest ever recorded for Surviving the Side Hustle back in May of 2023, he was the first guest brought back for a second tim...

You cannot build something meaningful while you are putting out fires. That one line from Joanna Zhang is the thing I could not unhear this week. In this Friday recap I pull out what stuck with me from the E217 conversation with Joanna Zhang, the operations strategist who basically invented the fractional VA model before anyone had a name for it. I get into her hot potatoes habit, delegating the b...

When a mentor kept asking Joanna Zhang why she really ran her business, one word finally fell out of her mouth and her tears dropped: unconditional love. That answer dissolved a blockage that years of smart strategy never could. Joanna is the founder of a fractional VA service, a plug and play team that fills the gaps in growing businesses, and an operations strategist whose model was later named...

"I'm not just their accountant, I'm their business partner." Justin Warren said that near the end of our conversation this week, and it reframed the whole thing for me. Justin is a partner at PKF O'Connor Davies, one of the top accounting and advisory firms in the country, and he co-leads the Stamford, Connecticut tax practice alongside a team of about 18. If you have ever been around public accou...

Justin Warren shut his life down for three and a half months a year, running 12 to 15 hour days while his wife held the house together and helped raise their kids. He is a partner at PKF O'Connor Davies, one of the top accounting and advisory firms in the country, and he walks Rob through what climbing to partner actually costs and how he keeps a life while doing it. The conversation covers how Ju...

At twenty five, Maria Garcia had a stroke that left her paralyzed from the nose down and unable to speak, communicating through finger taps and eye movements. It took fifteen years to claw her way back. Stem cells, hyperbaric oxygen therapy in Germany, every legitimate therapy she could reach. The thing that finally moved the needle was nutrition. In this Friday recap I pull out what stuck with me...

Maria Garcia had a stroke at 25 that left her paralyzed from the nose down and unable to speak, and it took a 15 year climb to get her life back. Nutrition is what finally moved the needle. Maria, a nutrition coach based in New Jersey who now helps clients worldwide, returns to Surviving the Side Hustle for a second conversation, this time about what happens after you survive the thing and realize...

Joe Rendina was making good money. By most measures he was doing fine, and yet he described it as a heaviness on his chest every single day, the slow grinding weight of being in the wrong seat. In this Friday recap I pull out what stuck with me most from my conversation with Joe: the torn ACL that started his path, how he built Iron Health Physical Therapy to four locations and what that speed rea...