Welcome to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.In today's episode, we take a moment to talk about taxes. In the midst of the 2026 tax season, it's easy to look on last year and think there's nothing that can be done or nothing to look out for. But in reality, there are regular, common mistakes that solopreneurs and small business owners make on their taxes. It's important to remember this, as you review your taxes and consider the impact for next year.Ryan shares three common issues he often sees on the self employed's tax return, so you can look out for it yourself or ask your tax preparer about it. At the end of the episode, Ryan also gives a quick review of Do Not Expect Too Much From the End of the World, and explains the insight he had watching this bleak look at the current working world.Subscribe and stick around, and in the meantime… keep grinding!Connect with Ryan Derousseau, CFP®, EAEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/  Website: https://thinkingcapfinancial.com/

On this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, sits down with author and freelance journalist Elaine Pofeldt to talk about what it really takes to succeed as a solopreneur.

Elaine has been running her solo business since 2007 and is the author of Tiny Business, Big Money and The Million-Dollar One-Person Business. She shares how building a solo business allowed her to be present while raising four children, and why she considers that flexibility one of the greatest rewards of working for yourself.

Together, Ryan and Elaine dig into the less-glamorous realities of freelance and solo work: uncertainty, discipline, financial resilience, taxes, health insurance, and the constant need to balance client work with business development. They also explore why so many people (at every life stage) are choosing the solopreneur path in search of freedom.

In this episode, you’ll learn:

• Why solopreneurs rarely feel “fully comfortable” — and why that’s normal

• How recurring clients and retainers build confidence and stability

• The importance of discipline, planning, and managing multiple roles

• Why living below your means creates resilience when clients disappear

• Smart ways freelancers can prepare for taxes and avoid surprises

• The biggest financial hurdle Elaine faced as a solo business owner

• Why “freedom” is the common thread driving people toward solo work

• How AI and technology are powerful tools for solopreneurs without capital

• Why freelancers often report better health than corporate employees

• The value of non-screen outlets and trusted “freelance buddies”

This conversation is a grounded look at solo business ownership… The trade-offs, the rewards, and the systems that make it sustainable over the long term.

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Connect with Elaine Pofeldt:

LinkedIn: http://linkedin.com/in/elainepofeldt/

YouTube: http://youtube.com/UCr5VUkqfMpz_JPGnnXu3F8a

Website: https://www.elainepofeldt.com/

Connect with Ryan Derousseau, CFP:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/ryanderousseau/

Website: https://thinkingcapfinancial.com/

Welcome to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.In today's episode, we look at how to simply get started in your new business - or growing your business to the next level. It's one of the hardest parts of the business journey: Simply starting. Too many times, we think too far ahead and it can overwhelm the process, destroying any effort to move forward. Ryan shares best practices for overcoming this concern, as it can set good ideas back for years or can lead to a very poor early efforts... until you learn what works. At the end of the episode, Ryan also gives a quick review of Predator: Badlands, and explains a lesson from the movie solopreneurs and small business owners can take away from the picture.Subscribe and stick around, and in the meantime… keep grinding!Connect with Ryan Derousseau, CFPEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

Welcome to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.In today's episode, we look at entity selection, particularly for small and service based businesses. What's the right business for you? LLC? Sole Prop? S-Corp? Ryan shares best practices for the selection, and explains why you should use the entity choice as a tool - not a signpost to reach. That's because there are good reasons for each entity and downsides to the same business structure. And you will have to operate in it moving forward, depending on which one you select. At the end of the episode, Ryan also provides a movie selection for those in solo business - and this time he takes a quick look at The Mastermind.Subscribe and stick around, and in the meantime… keep grinding!

Connect with Ryan Derousseau, CFP®, EA

Email: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

Welcome back to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.

This episode is a reboot of the show and a quick reset on what you’ll hear here and who it’s for: solo operators and very small business owners — therapists, private practice doctors, engineers, marketers, tinkerers, and side entrepreneurs — who are building a business (and a life) on their own terms.

Ryan shares why he loves working with this crowd, how his own solo-operator mindset shapes the show (including compliance through United Financial Planning Group), and why his firm is called Thinking Cap Financial.

This isn’t a “tech billionaire” podcast. It’s for grinders, innovators, and go-getters who want freedom, meaningful work, and the ability to afford the lifestyle they actually want — without needing a boss.

Going forward, you’ll see two episodes per month:

✅ Entrepreneur interviews (journey, routines, what keeps them moving)

✅ Solo business & money tips directly from Ryan (uncertainty, growth, and sustainable success)

Subscribe and stick around, and in the meantime… keep grinding!

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Connect with Ryan Derousseau, CFP

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/ryanderousseau/

Website: https://thinkingcapfinancial.com/