Tax Hacks for Entrepreneurs with Neil Jesani

What if one early paperwork choice cost you millions later?

I walked away from this conversation feeling oddly relieved and slightly alarmed. Relief because a clear set of rules can turn tax complexity into predictable moves. Alarm because most entrepreneurs treat taxes like an afterthought—until a missed step becomes a multimillion-dollar problem.

Why entity planning is a strategic decision, not just legal paperwork

Think of entity selection as the scaffolding for whatever you plan to build. Set it right and you gain flexibility, outside capital access, and favorable tax windows. Get it wrong and you can lose benefits like qualified small business exclusions or make fundraising awkward. The practical rule of thumb offered here is simple: start as an LLC if it’s a side hustle, elect S corporation tax treatment once you have traction, and form a Delaware C corporation if you intend to raise institutional capital.

That last part matters. A Delaware C corp gives you an employee option pool, easier outside investment, and structural advantages for scaling. But it’s not a one-size-fits-all answer—your goals determine the right structure.

The single mistake high-earners keep repeating

Most entrepreneurs focus on two things: new revenue opportunities and crisis avoidance. Taxes rarely make the list. That’s the real missed opportunity. When taxes are planned into growth, entrepreneurs unlock strategies unavailable to W-2 workers—retirement vehicles, entity-level elections, and clever deductions that materially change cash flow.

My immediate takeaway: make tax planning part of momentum-building. Once revenue ramps, call the right advisor and put strategies in place before year-end. Waiting tosses potential savings out the window.

Estate planning: imperfect plans beat perfect procrastination

There’s a moral gravity to estate planning that makes people delay it. The blunt truth here is that a solid, not perfect, estate plan protects family wealth and reduces tax friction later. You don’t need every detail ironed out to start. Draft the documents with qualified counsel. Name trustees and beneficiaries. Make decisions and iterate.

Even more urgent than wills and trusts is asset protection. Lawsuits and creditor claims can wipe out a lifetime’s work while you’re still alive. Asset protection acts as a firewall; estate planning preserves how that wealth passes on.

Real estate: don’t buy for tax benefits—let benefits be a bonus

That line stopped me. Treat real estate as an investment first and a tax vehicle second. If a property doesn’t make sense financially without depreciation, don’t buy it for deductions alone. That keeps decisions rooted in returns rather than tax chases.

But the tax mechanics are powerful if you qualify to use them. Residential properties depreciate over 27.5 years, commercial over 39.5. Cost segregation studies let you accelerate depreciation and, with current rules, take substantial bonus depreciation immediately. The catch is in utilization: passive losses often can’t offset active W-2 income unless you qualify as a real estate professional.

• Real estate professional status: requires 750 hours/year and that those hours exceed other work activities.
• Short-term rental loophole: 100 hours threshold can allow otherwise busy entrepreneurs to convert passive depreciation to active deductions.

Those small-sounding numbers—750 and 100—are the difference between seeing a tax benefit now or only on paper. For busy founders, short-term rentals can be a surprisingly accessible bridge.

Actionable tax architecture—practical moves that change outcomes

Three moves stood out. First, align entity choice with your exit and funding plan. Second, treat tax planning as part of growth playbooks, not a year-end scramble. Third, pair estate planning with asset protection early, because you can’t transfer what you’ve already lost to creditors or judgments.

There’s also a mental model that stuck with me: buy real estate as if you won’t get a tax break. If it still returns, then tax rules make it much sweeter. That mindset prevents speculative decisions driven by optimistic accounting.

My favorite surprising facts

• Cost segregation can often reclassify 20–25% of a property’s value for immediate depreciation.
• Bonus depreciation rules can allow near-immediate write-offs on reclassified assets.
• Short-term rental rules lower the bar to turn passive losses into active ones—only 100 hours required.

Honestly, I didn’t expect the real estate professional test and the 100-hour short-term rental exception to be such practical levers. They’re not arcane rules for accountants; they can change the cashflow math for many entrepreneurs.

Closing thoughts

Taxes feel like a maze until you map them to business goals. Entity selection, estate and asset protection, and real estate treatment are all levers you can tune today. Start imperfectly. Prioritize asset protection. Think like a long-term investor, not a year-end planner.

And if there’s one quiet ambition here—it’s this: take a little of the entrepreneurial bravery you apply to product and sales, and apply it to your tax and estate plans. The payoff is cumulative and, years later, often life-changing.