Why Ready Founders Don't Wait Until Filing Season
Originally published in May 2025 as part of The Ready Founder™ newsletter. Subscribe to get financial leadership insights delivered monthly to help you gain the clarity and confidence you need to scale successfully.
As the dust settles from another tax filing season, many founders are breathing a sigh of relief, putting taxes out of mind until next year's deadline looms. But at One Degree Financial, we've observed that Ready Founders™ take a different approach.
Most business owners think about taxes only when they're forced to: during filing season or when facing an unexpected tax bill. This reactive approach costs growth-stage companies thousands, sometimes tens of thousands, in unnecessary tax payments every year.
Ready Founders™ understand that tax planning is a year-round discipline that directly impacts cash flow, profitability, and even exit value.
A Personal Lesson: Why Exit Planning Can't Wait
Back in 1999, I learned this lesson the hard way with my first tech company.
When our company was being acquired, I was young and didn't know what I didn't know about tax planning for an exit. By the time the transaction closed, it was already too late to implement strategies that could have saved us money.
How much money? Enough to have paid for both of my children's college educations.
The painful truth was that by not planning ahead for the tax implications of our exit, we left significant money on the table. This was money that should have benefited our families and futures. It wasn't until after the deal closed that I realized what we had missed.
That expensive lesson shaped my approach to business forever: to be prepared is to make a world of difference. It's why we're so passionate about helping founders become Ready Founders™ who have the financial clarity and confidence to maximize value at every stage of their journey, especially when it comes time to exit.
Why Year-Round Tax Planning Matters Now More Than Ever
The tax landscape for SaaS and tech companies has grown increasingly complex, with opportunities and pitfalls that change frequently:
R&D credits that could save six figures annually but require proper documentation throughout the year
Entity structure decisions that significantly impact your tax burden as you scale
Compensation strategies that can dramatically shift your personal and business tax position
State nexus issues that create unexpected tax liabilities as you expand your customer base
These aren't just administrative concerns. They directly impact how much capital you retain to fuel growth.
What Ready Founders™ Do Differently
Ready Founders™ don't just comply with tax laws; they actively shape their tax strategy by:
Forecasting tax liabilities quarterly and integrating them into cash flow planning
Structuring compensation (salary, distributions, equity) with tax efficiency in mind
Evaluating major business decisions through a tax impact lens before execution
Maintaining proactive strategies for potential exit-related capital gains
Working with financial advisors who understand their specific industry's tax nuances
The Cost of Reactive Tax Planning
Consider these common scenarios we see with founders:
A SaaS company discovering they could have saved $85,000 in R&D credits, but only after it's too late to properly document
A founder who sells their business only to realize their entity structure is costing them 15% more in taxes on the transaction
A high-growth company surprised by a $175,000 tax bill because they didn't forecast based on their rapid growth
In each case, the founder had options, if they'd planned ahead.
Start Your Strategic Tax Planning Now
Improve Cash Flow, Fund Growth, Attract Investors
As we move into the second half of the year, this is the perfect time to reset your approach to tax planning. Here are three immediate actions you can take:
Schedule a mid-year tax projection based on your current growth trajectory
Review your entity structure to ensure it still aligns with your business goals
Evaluate your compensation strategy for tax optimization opportunities
Remember: Every dollar saved in taxes is a dollar that can fund your growth. That's why Ready Founders make tax strategy an ongoing priority, not a once-a-year scramble.
Ready to Stop Leaving Money on the Table?
Is your business prepared to maximize tax advantages this year? Or are you leaving money on the table? I learned my lesson the hard way. You don't have to.
Ready to stop leaving tax money on the table and start planning strategically? Book a Readiness Call with us today to discuss how to optimize your tax position for growth and future exits.
About the Author: Rod Loges is CEO of One Degree Financial and host of the MILCOM Founders podcast, where he helps veteran entrepreneurs build businesses with strong financial foundations.
The Ready Founder™ is part of One Degree Financial's commitment to helping founders gain the financial clarity and confidence they need to scale successfully. Learn more at onedegreefinancial.com.
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