🎥 Watch the Episode
📌 Quick Summary
In this episode, Jacob Dean shares his path from small-town Ohio to becoming a tax attorney, law clerk, business lawyer, and eventually an entrepreneur running his own firm. His story highlights the power of strategic risk-taking, understanding your passions, and building a business that reflects your experience and values.
❓ Common Questions & Answers
Q: What inspired Jacob to pursue law after studying finance?
A: He wanted a versatile degree that opened more doors than it closed — and law offered that.
Q: Why did he leave P&G?
A: To grow as a tax professional, pursue additional credentials, and accept the opportunity to clerk at the U.S. Tax Court.
Q: What was the turning point that pushed him into entrepreneurship?
A: Turning 40 and realizing he was ready to build something of his own instead of only advising others.
Q: What is his advice for new business owners?
A: Get good help — don’t try to build everything alone.
📜 Step-by-Step Guide
-
Explore broad interests early.
Jacob used undergrad to test finance, law, and sciences. -
Say yes to opportunities that expand your skills.
Working at P&G gave him real-world exposure to large-scale operations. -
Invest in advanced learning.
Clerking at the U.S. Tax Court and completing an LLM broadened his expertise. -
Work across business environments.
Both firm and in-house roles helped him understand business operations at every level. -
Reflect intentionally at major milestones.
Turning 40 sparked a thoughtful evaluation of long-term goals. -
Launch with strategy, not impulse.
Jacob built his firm using the same advice he gave clients for years.
📖 Historical Context
Tax law, business formations, and corporate structures have evolved dramatically since the early 2000s. Jacob’s career coincided with:
-
The 2008 economic downturn
-
Shifts in tax policy
-
Growth of corporate in-house legal departments
-
A rise in entrepreneurship and small business formation
These shifts made versatility and business awareness crucial for modern attorneys.
🧭 Guest Journey Summary
Jacob grew up in Wooster, Ohio, surrounded by educators. After studying finance and navigating a difficult job market, he chose law school for its flexibility. He worked at P&G’s tax department, clerked for the U.S. Tax Court, and later joined firms in D.C. and Ohio. Over time, he realized he loved the business side of law just as much as the legal side. After moving west and engaging in deep reflection, he launched his own firm to help entrepreneurs build stronger businesses with tax-informed guidance.
🏢 Business Competition Examples
Firms competing in Jacob’s area typically include:
-
Traditional tax-focused law firms
-
Business formation specialists
-
Fractional general counsel services
-
Accounting firms offering business advisory
-
Online legal platforms providing DIY templates
Jacob differentiates himself through combined tax + business strategy expertise, which many competitors lack.
💬 Discussion Section
Jacob’s story reveals an important theme: career paths are rarely linear. His progression from finance to law to tax to entrepreneurship shows the value of developing layered skills. Many professionals underestimate how much business understanding helps them serve clients more effectively. Jacob emphasizes that legal work is only part of being a successful attorney — the rest is client development, operational strategy, and leadership.
His approach also challenges the traditional law firm mindset of slow, conservative growth. Instead, he views a firm as a business first, law practice second — allowing for more strategic scaling.
⚖️ The Debate
Should law firms operate like traditional businesses or maintain the conservative, slow-growth model?
Traditional View:
-
Controlled growth reduces risk
-
Lawyers should focus primarily on legal work
-
Business activities dilute professionalism
Modern View:
-
Strategic growth prevents burnout
-
Firms must innovate to remain competitive
-
Clients expect streamlined experiences and business-oriented advice
Jacob leans toward a balanced modern approach: grow intentionally, think like a business leader, and serve clients with both legal and operational insight.
✅ Key Takeaways
-
Your background doesn’t limit your entrepreneurial potential.
-
Law is a versatile platform that opens many career paths.
-
Business operations matter just as much as legal expertise.
-
Strategic reflection at mid-career can reveal your true direction.
-
Don’t build alone — get good help.
⚠️ Potential Business Hazards
-
Over-relying on legal skills without understanding business fundamentals
-
Hiring too slowly or too reactively
-
Failing to price services strategically
-
Letting fear drive major career decisions
-
Ignoring tax implications during business planning
❌ Myths & Misconceptions
-
Myth: Starting a firm means you’ll make more money immediately.
-
Myth: Lawyers who focus on business are “less serious.”
-
Myth: If you don’t take a job opportunity, you’ll never get another.
-
Myth: Entrepreneurship is only for extroverts.
📚 Book & Podcast Recommendations
-
The E-Myth Revisited – Michael Gerber
-
Built to Sell – John Warrillow
-
Atomic Habits – James Clear
-
Firm Learning podcast
-
The Business of Law podcast
⚖️ Legal Cases
Relevant cases for tax and business practitioners:
-
Chevron U.S.A. v. Natural Resources Defense Council – administrative interpretation standards
-
Commissioner v. Duberstein – defining “gift” under tax law
-
Moline Properties v. Commissioner – corporate separateness
-
Salomon v. Salomon – foundational case on corporate identity
📣 Expert Invitation
If you're a founder, entrepreneur, or expert with a story worth sharing, we’d love to have you on the show.
Learn more at inventiveunicorn.com or schedule time at strategymeeting.com.
🔚 Wrap-Up Conclusion
Jacob Dean’s journey shows the power of thoughtful decisions, diverse experiences, and the courage to take ownership of your career. His blend of tax knowledge, business strategy, and entrepreneurial passion makes his story a valuable guide for anyone looking to build a meaningful business on their own terms.
