Optimizing Success: Defining Your Solvable Problem and Achieving True Wealth with Dan Nicholson

In this episode, Sheila Slick interviews Dan Nicholson, who shares his journey from a young entrepreneur to a successful CPA and author. Dan’s story highlights his early start in the business world, leading to a significant career shift at UPS that steered him towards accounting. His experience laid the groundwork for his own CPA firm, where he encountered the challenges and rewards of entrepreneurship.

Dan discusses the core strategies from his book, “Rigging the Game,” emphasizing the importance of optimizing over maximizing in small business and defining a solvable problem that aligns with personal wealth goals. He introduces the concept of different wealth types, their risks, and the importance of focusing on net worth and financial optimization.

Don’t miss this insightful conversation on achieving certainty and success in an ever-changing economic landscape.

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Key Takeaways:

Defining Milestone Moments:

Dan’s early entrepreneurial spirit and career shift to accounting were pivotal in shaping his professional path.

Optimizing Over Maximizing:

Focus on optimization rather than maximization in business to ensure sustainable growth and personal satisfaction.

Solvable Problem:

Identify a unique definition of wealth based on personal goals and timelines, referred to as the solvable problem.

Understanding Wealth Types:

Recognize different wealth types (hustlers, gamblers, optimizers, savers) and manage associated risks accordingly.

Financial Management:

Emphasize recovering unnecessary expenses, saving on taxes, and ensuring liquidity and solvency for business scaling.

Tools and Resources:

Utilize tools like CertaintyApp to calculate financial needs and monitor progress towards goals.

Personal Alignment:

Ensure that business goals align with personal aspirations for a balanced and fulfilling life.

Conclusion: Dan Nicholson shares valuable insights into achieving success by focusing on financial optimization and aligning business efforts with personal goals. His journey underscores the importance of defining and pursuing a solvable problem to achieve true wealth and fulfillment.

Welcome to Milestone Moments, the podcast where we delve into the journeys that lead to success. I’m Sheila Slick, your host and founder of Five Milestones. Each episode brings you insights from entrepreneurs, leaders, and experts who share their milestone moments—those pivotal events that have reshaped their journeys and led to significant achievements. If you’re seeking motivation, you’re in the right place. Subscribe now and discover the milestones that mark the path to success.

Today’s Episode: Dan Nicholson’s Journey to Entrepreneurial Success

In this episode, I’m thrilled to introduce Dan Nicholson, a serial entrepreneur and founder of Nth Degree CPA, an accounting and financial consulting firm. Dan is the author of Rigging the Game: How to Achieve Financial Certainty, Navigate Risk, and Make Money on Your Own Terms, a bestseller recognized by USA Today and the Wall Street Journal. Named a top 40 under 40 in accounting globally four times, Dan has created and run multiple small businesses, including CertainTU and CertainTNews, a platform syndicated to over 1 billion monthly users. He also hosts the Rigging the Game podcast and serves as a consulting producer for PBS Opportunity Knox. Welcome to the podcast, Dan.

A Defining Milestone: The UPS Opportunity

Sheila: Dan, was there a milestone moment, a catalyst that led you down this career path?

Dan: Absolutely, Sheila. Growing up, I was always the kid with a new business idea every week, though most of them were bad. I went to college intending to major in marketing, which surprises people given my career in accounting and finance. As the first person in my family to attend college, I was commuting, living at home, and borrowing money for tuition.

One day, I received an email about a scholarship opportunity from UPS. They were hosting a career fair, and I saw it as a chance to get a foot in the door in a marketing position while securing some much-needed scholarship money. I showed up at the career fair in a suit, only to find myself in a room full of people in casual clothes. The fair was primarily for manual labor positions in the UPS hub, but I approached some finance guys with my resume, hoping to learn about any marketing internships.

Despite initial confusion, they saw potential in me and mentioned a part-time finance supervisor position. At 19, I landed that job, managing 20-25 people. This experience gave me the confidence that I could achieve anything and set me on the path to changing my major to accounting. This pivotal moment ultimately led to a fellowship at the board that writes all the accounting standards in the US, which dramatically shaped my career.

The Shift to Entrepreneurship

Sheila: And then you founded your own CPA firm?

Dan: Yes, after years of prestigious roles and gaining invaluable experience, I realized my true passion was entrepreneurship. Despite a great resume and a stable income, I wasn’t happy. I wanted to be an entrepreneur. Eventually, I found a way to reconcile my accounting expertise with my entrepreneurial spirit, leading me to start my own firm.

Strategies for Winning in Business and Life

Sheila: Your book and podcast are fantastic resources for entrepreneurs. Can you share some of your top strategies for winning in business and life on our own terms?

Dan: Certainly. My book is essentially my operating system—a set of principles for winning in business with less effort and risk. One key realization was understanding the difference between maximizing, which is what large corporations do, and optimizing, which is crucial for small businesses. Fortune 500 companies focus on maximizing shareholder value, which involves having the most of everything. Small business owners, however, need to optimize—focusing on the most important priorities with the resources at hand.

A central concept in my book is the “solvable problem,” which is your unique definition of wealth. You take all your goals, assign them dollar values and timelines, and calculate how much more you need to make to fund those goals. This approach gives you a clear path and helps avoid the trap of constantly striving for “more” without a clear end goal.

Practical Steps to Achieve Your Goals

Sheila: How do you help entrepreneurs solve this issue and optimize their path?

Dan: First, get clear on your solvable problem using tools like the one at certaintyapp.com. This helps you measure your progress accurately. Next, focus on increasing your net worth. Many business owners have seen their net worth decline due to debt, so it’s crucial to reengineer your expenses and recover unnecessary spending, especially on taxes. Lastly, reposition your financials to ensure liquidity and solvency, which allows you to scale your net worth and fund your goals efficiently.


These strategies are about making your business work for you, not the other way around. By recovering expenses, reducing unnecessary tax payments, and repositioning your financials, you can grow your net worth and achieve your personal and professional goals.

Stay tuned for more insightful conversations on Milestone Moments. If you found today’s episode valuable, subscribe and share it with others who might benefit from Dan’s wisdom. Until next time, keep striving for your milestone moments.

Financial Freedom, Wealth Building, Entrepreneurial Success, Intentional Decisions, Profitability, Business Strategies

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