What do you do when you’re young and at a career crossroads with no desire to work for someone else but no savings or credit rating to launch a business? If you’re Rob*, you take a deep breath, seek borrowing alternatives and start building. From a small auto body shop made possible by grit and a savvy tax strategy, Rob would go on to create a multi-location business empire, backed not by venture capital or bank loans but by shrewd financial structuring and the relentless drive of a smart operator.

This case study follows Rob’s journey from a young man with little more than ambition to a multimillionaire with multiple business exits, real estate income and a robust retirement plan. But it’s not just Rob’s story. It’s also the story of how Ascend partner Martin Belak-Berger strategically guided him through each step. From note financing and asset structuring to cost segregation studies and pension planning, every move was intentional and tax-savvy.

A strategic sale and a bankrupt beginning

It all started with a different client. An established auto body shop owner preparing to sell his business to a national consolidator. Two offers were on the table. Both included a mix of cash and equity in the consolidator’s stock. One offered a lower sales price but more cash; the other dangled higher numbers on paper, but more of the value was tied up in stock.

Martin’s advice? Don’t bet the house on equity in a business you can’t control. “If the cash price is something you’re happy with, take the deal and consider any stock a bonus,” Martin advised.

It was the right call. Within three years, the consolidator went bankrupt, rendering the stock worthless. However, the client had already pocketed the cash and, surprisingly, ended up reassembling his old team and building a new chain, which eventually led to a second profitable sale.

And it’s here that Rob entered the picture.

Career crossroads: a risky leap

Rob had worked for that same consolidator before it went under. With the business gone, he had a choice: work for someone else or try to do it on his own. He chose the latter. The only problem? He had no savings. No business credit. No traditional financing options. Just an idea and a contact: the former shop owner who told him, “You’ve got to go and see Martin and Scott [Belak-Berger and Eisner, who later went on to found Ascend].”

Martin sat down with Rob and helped him assess the opportunity. He had his eye on a small body shop for sale, but the path forward wasn’t obvious. A traditional bank wouldn’t lend to a first-time owner with no track record. SBA (Small Business Administration) loans were technically an option, but they came with much higher costs, extensive paperwork, and extended timelines.

Instead, Martin recommended a seller-financed transaction, a strategy that would become foundational to Rob’s rise.

The note: a foot in the door

Under Martin’s guidance, Rob proposed a deal to the seller where they would finance the purchase through a ‘note’. In exchange for a modest down payment, which Rob scraped together via hard money and personal connections, Rob would take over the business and pay the rest in installments. The body shop itself, along with the property, would serve as collateral.

For sellers, this type of arrangement can seem risky, but Martin made a compelling case. The seller would receive a competitive interest rate (often higher than a bank CD), and by structuring the deal as an installment sale, the seller could defer capital gains taxes over the life of the loan. Given that no other offers were on the table, it was a win-win solution.

And for Rob, it was everything. The deal gave him his first foothold as an owner and laid the foundation for everything that came next.

Innovative structures, smarter tax

Even before the ink dried, Martin was shaping Rob’s path for maximum protection and tax efficiency. First, he ensured he wasn’t buying company stock, only assets. Why? Because stock purchases transfer all the company’s historical liabilities to the buyer. In the auto body business, that can mean inherited environmental risks, workplace injury liabilities, or customer claims. An asset purchase gave Rob a clean slate.

Second, they separated the purchase of the business from the purchase of the property. Martin and Rob created two separate entities: one to own and operate the shop, the other to hold the real estate. This offered multiple advantages:

• Liability protection (so a slip-and-fall lawsuit at the shop wouldn’t jeopardize the property).
• Tax flexibility (allowing different treatment for income and depreciation).
• Long-term wealth creation (property ownership offered passive income and appreciation potential).
  

To further reduce Rob’s tax burden, Martin recommended a cost segregation study on the property, allowing for accelerated depreciation. By breaking down the property into individual components — equipment, fixtures, electrical systems — Rob depreciated much of the asset in the first few years. By accelerating depreciation, he was able to offset earnings from the shop with losses from the building, thereby helping him retain more of his cash during those critical early stages.

Growth mode: shop number two

A couple of years in, Rob was back. His first shop was thriving. He’d built essential relationships with insurance carriers, created an efficient workflow, and established himself as a strong operator. Now, he had his eyes on a second shop, much larger than the first.

Martin repeated the winning formula. Seller note. Separate entities for real estate and operations. Asset purchase to avoid liability. Cost segregation study to boost early-year depreciation.

But this time, they added another layer: a purchase price allocation. By carefully assigning value to specific assets, such as machinery, paint booths, and equipment, and allocating the remainder to goodwill, Rob structured the deal for optimal tax treatment. Goodwill is amortized over 15 years; equipment, on the other hand, can often be depreciated more quickly, allowing for more immediate tax relief.

Rob’s real estate entity now had significant depreciation losses while the operating business was generating substantial profits. With another strategic move, Martin elected to treat both entities as one for tax purposes, allowing Rob to offset income from one with losses from the other.

As the business scaled, tax planning became even more critical.

Building wealth and a pension

Rob’s income was climbing, but so were his obligations: payroll, property loans, and equipment purchases. To ease the tax burden and start planning for the future, Martin introduced a defined benefit pension plan. At the time, it was a relatively new type of pension plan, now much more common, that allowed Rob to contribute significantly more than a conventional plan.

Because the plan was age-weighted, Rob could contribute a significantly larger amount for himself than for his younger employees. Contributions were tax-deductible, and unlike simpler retirement plans, a defined benefit plan allowed for substantial annual deposits.

This strategy created a significant tax shelter, added to Rob’s long-term retirement security, and helped attract employees in a competitive hiring environment.

The exit and the passive income play

Eventually, Rob received an offer he couldn’t refuse. Another consolidator wanted to buy his businesses. But thanks to the thoughtful entity structures Martin had put in place, Rob had options.

He sold the operating companies but kept the real estate. Now, his former businesses became tenants, paying rent to Rob each month.

Rob also optimized the transaction itself:

• Most of the gain was treated as long-term capital gain.
• Ordinary income exposure was minimized.
• The properties remained untouched, generating consistent passive income.
  

With pension assets, real estate cash flow, and no immediate debt, Rob was financially secure. He even worked with the new owners for a few years before ultimately stepping away from the role. You think this is the ending, right? Not quite!

Back in the saddle: scaling for the next chapter

A couple of years after his big exit, Rob was back on the phone with Martin. Retirement hadn’t stuck. He’d partnered with another operator who already owned a few shops, and Rob dove straight in to help restructure operations and improve performance.

Soon after, Rob indicated he was eyeing additional shops. The plan? Package multiple locations together and prepare for another potential sale. As he put it, three shops was a good start, but if they could grow the group to six or eight, they’d be able to attract a different calibre of buyers.

If his past is any guide, Rob is likely to continue leaning on the tax-smart playbook that got him here: structuring deals with care, managing risk and building toward long-term value.

Final thoughts: a trusted advisor, a structured future

Rob’s journey is the blueprint for what’s possible when ambition meets good advice and trusted expertise. He didn’t start with wealth. He didn’t have investors. He built from the ground up, leveraged to the gills, betted on himself, and made every dollar stretch.

But he didn’t do it alone. At each turn, Martin guided him as a strategic partner, not just on taxes but on entity formation, financing options, cash flow planning, and long-term growth.

The result? A real estate portfolio worth millions. A pension plan that secures retirement. Businesses that generated income rather than capital gains. And a client who’s not just thriving but giving back, mentoring others, and even buying a group of nuns a much-needed new van to carry out their good work!

This is what it looks like when tax strategy becomes life strategy, as structure builds wealth. And when the right advisor can change everything.

*Client name changed to protect their privacy