Side Hustle Pro

If you’re a side hustler or solopreneur, taxes can go from simple to overwhelming real fast and the truth is, many entrepreneurs are quietly losing thousands of dollars just by not knowing what they don’t know.

In this episode, I sat down with CPA and TurboTax Expert Lisa Greene-Lewis to break down the most common tax mistakes side hustlers make, from choosing the wrong business structure too early to missing out on key deductions and failing to stay organized throughout the year. We also unpack what actually makes taxes more complex as your business grows and how to stay ahead of it before tax season hits.

This conversation is all about helping you feel more confident, more prepared, and more in control of your finances. Because the goal is not just to make money in your business but to keep more of it.

Main Takeaways
Lack of consistent tracking is the biggest mistake that leads to overpaying taxes
Many solopreneurs miss deductions simply because they are unaware of what qualifies
Staying organized year-round is the key to reducing stress and maximizing savings

Highlights Include
00:00 – Introduction to tax season for solopreneurs
02:00 – Lisa’s journey into tax expertise and entrepreneurship
05:20 – LLC vs S corp: what you actually need to know
08:20 – When taxes start to feel complicated
09:30 – Why tracking income and expenses is critical
11:40 – Common deductions people miss
13:00 – Home office deduction explained
14:20 – Section 179 and equipment write-offs
15:10 – What you can’t deduct (clothes, hair, makeup)
16:40 – Business credit card interest deduction
17:20 – Employing your kids as a tax strategy
18:00 – SEP IRA and retirement savings for entrepreneurs
19:00 – Qualified Business Income deduction
20:10 – Key tax law updates and 1099-K changes
23:20 – How to stay organized with QuickBooks
25:40 – How TurboTax experts support business owners
27:10 – Lisa’s personal system for staying organized

Links Mentioned in This Episode
TurboTax: https://turbotax.com/business
QuickBooks: https://quickbooks.intuit.com

Watch & Listen
Watch this episode on YouTube and listen on all podcast platforms:
Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
YouTube: https://www.youtube.com/sidehustlepro

Announcements
If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
Save your seat here.

Social Media
LinkedIn: https://www.linkedin.com/in/lisa-greene-lewis-7721b815a
Website: https://turbotax.com/business

Side Hustle Pro – @sidehustlepro
#SideHustlePro
Hosted on Acast. See acast.com/privacy for more information.

If you’ve been waiting for the perfect moment to finally start that thing you said you’d do this year, this episode is your wake-up call. Because the truth is, that moment isn’t coming.

This week, I’m pulling back the curtain on a very real, very messy week in my life and sharing why I decided to hit record anyway. From sick kids to mental clutter to a house that is far from organized, I had every reason to wait. But instead, I leaned into a powerful reminder: progress doesn’t require perfection.

In this episode, I walk you through the mindset shifts that have helped me move through overwhelm, take action with limited time and energy, and stop letting the idea of “feeling ready” delay my goals. Because sometimes the real work isn’t the task itself, it’s learning how to show up before everything feels aligned.

Main Takeaways
Waiting for the perfect time will keep you stuck longer than just starting messy
You have to work with the time and energy you actually have, not what you wish you had
Naming what’s holding you back helps you move through it faster
The real growth often comes from managing your mindset, not completing the task

Highlights Include
00:00 – Why I recorded this episode despite not feeling ready

02:10 – How “unexpected” life moments keep disrupting plans

04:18 – Learning to work in chaos instead of waiting for order

05:30 – Lowering the bar to get started

06:10 – Work with the time you have, not the time you wish you had

08:00 – Managing your energy to show up at your best

10:15 – Why naming the problem helps you move forward

11:43 – Recognizing the season you’re in and adjusting expectations

14:00 – Are you truly blocked or just thrown off?

16:12 – How accountability helped me launch Side Hustle Pro

18:36 – Overcoming imposter syndrome in a career leap

21:22 – The hidden cost of needing to “have it all together”

23:21 – Why perfection delays your income and growth

26:24 – Maybe the real goal is mastering your mindset

29:19 – Adjusting expectations so you can move forward

Links Mentioned in This Episode
Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 10th)

Watch & Listen
Watch this episode on YouTube and listen on all podcast platforms:
Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
YouTube: https://www.youtube.com/sidehustlepro

Announcements
If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
Save your seat here.

Social Media
Side Hustle Pro – @sidehustlepro
#SideHustlePro
Hosted on Acast. See acast.com/privacy for more information.

One of the biggest misconceptions I see when it comes to making money is the belief that you need to start from scratch. A new certification, a brand new idea, or a completely different skill set. But the truth is, most of us already have everything we need. The real problem is not a lack of knowledge, it is not knowing how to package and position what we already know.

In this episode, I break down five simple and practical ways to turn your existing skills, experiences, and knowledge into income. Whether you are in between roles, exploring a side hustle, or just trying to make extra money right now, this episode is your reminder that there is value in what you already bring to the table.

I also walk through a key mindset shift. You do not need to be the top expert. You just need to be a few steps ahead of the person you are helping. People are not just paying for information. They are paying for clarity, speed, guidance, and confidence. And that is where your opportunity lies.

Main Takeaways
You do not need new skills or certifications to start making money
There are five core ways to monetize what you already know
People pay for clarity, speed, and guidance, not just expertise
Start with one path and keep it simple instead of trying everything

Highlights Include
00:00 – The biggest misconception about making money
01:30 – Why you already have valuable, monetizable knowledge
02:00 – The 5 ways to make money with what you know
03:00 – The mindset shift you need before starting
04:00 – Service and coaching as the fastest path to income
06:00 – Done-for-you services and why people pay for convenience
08:00 – Creating simple digital products that sell
10:30 – Workshops and why people pay for real-time learning
13:00 – Why reminders are key when selling anything
15:00 – Using content to create opportunities and income
18:00 – How to use AI without losing your voice
21:00 – Why you should pick ONE path and start now

Links Mentioned in This Episode
Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, March 20)

Watch & Listen
Watch this episode on YouTube and listen on all podcast platforms:
Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
YouTube: https://www.youtube.com/sidehustlepro

Announcements
If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
Save your seat here.

Social Media
Side Hustle Pro – @sidehustlepro
#SideHustlePro
Hosted on Acast. See acast.com/privacy for more information.

This week in the guest chair is Chanel Tyler, a strategist, creator, and self-described “contentpreneur” who has worked across investment banking, luxury marketing, and YouTube before stepping fully into entrepreneurship.

Chanel built her reputation online by sharing trusted product recommendations and insights from her background in beauty marketing. But after years of consulting with a creator commerce platform that generated over 80% of her income, everything changed when the company suddenly shut down.

In this episode, Chanel opens up about what it really looks like to rebuild after losing the majority of your income overnight. She shares how she pivoted by diversifying her platforms, leaning deeper into affiliate marketing, launching new creator education programs, and embracing the vulnerability of sharing her personal story — including her journey with hearing loss.

If you’ve ever worried about relying on a single income stream or wondered how creators actually make money online, Chanel breaks down the strategy behind building a sustainable creator business.

In this episode, Chanel shares:
How she built a creator business by combining corporate strategy, content creation, and affiliate marketing
What happened when the platform responsible for 80% of her income shut down overnight and how she rebuilt
Why diversification across platforms, income streams, and partnerships is essential for creators and entrepreneurs
How affiliate marketing works and how creators can use performance data to negotiate higher-paying brand deals

Highlights Include
00:00 – Introduction
02:10 – Chanel’s career path from investment banking to luxury beauty marketing
05:10 – Building an audience through skincare and product recommendations
09:00 – Landing a role at YouTube working with top creators
15:00 – Saving a year of income before leaving corporate
19:00 – The moment she lost 80% of her income overnight
24:30 – Why diversification is critical for creators and entrepreneurs
27:00 – Building content series that grow an audience
32:00 – Affiliate marketing vs. brand partnerships explained
37:00 – Sharing her journey with hearing loss and disability
40:00 – How statement earrings became part of her empowerment story
43:00 – Affiliate income strategies for creators

Links Mentioned in This Episode
• Substack: Sensible
• Julia Broome
• Check out the Networth and Chill Podcast;Creator Economy & Brand Deals with Victoria Paris
• ShopMy: https://shopmy.us/home/creators
• MagicLinks: https://www.magiclinks.com/creators
• BrandCycle: https://brandcycle.com/
• LTK: https://company.shopltk.com/en/creator
• Nordstrom Affiliate Program: https://www.nordstromcreators.com/
Check out Chanel’s Creator Profit Lab’s interest form & course registration
Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, March 20)

Watch & Listen
Watch this episode on YouTube and listen on all podcast platforms:
Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
YouTube: https://www.youtube.com/sidehustlepro

Announcements
If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
Save your seat here.

Social Media
Instagram: @thecreatorprofitlab
Instagram: @buymechanel

Side Hustle Pro – @sidehustlepro
#SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

This week in the guest chair is sales and business coach Dielle Charon, founder of For the 23%, where she helps women of color build profitable businesses and grow their income through coaching and entrepreneurship.

Dielle shares how she went from earning $2,500 a month as a social worker with six-figure student loan debt to building a multi-seven-figure coaching business. Along the way, she explains why traditional jobs often undervalue your skills, how to identify the expertise you can monetize, and why the coaching industry continues to grow despite criticism.

In this conversation, we also dive deep into the mindset shifts needed to move from six-figure income to seven-figure business growth, including overcoming people-pleasing, claiming your expertise, and stepping fully into your authority.

If you’ve been thinking about turning your knowledge into income, starting a side hustle, or scaling your existing business, this episode will help you see what’s possible.

Highlights Include
00:00 – Why Dielle realized her corporate career wasn’t the life she wanted
05:30 – Testing multiple side hustles before finding the right one
08:00 – How to identify skills you can monetize
12:00 – Why the coaching industry gets criticism and why it’s still growing
16:30 – The truth about selling and why everyone is already selling themselves
20:00 – Why your job isn’t amazing — you are
23:45 – Breaking the mindset barriers around charging for your expertise
25:50 – The biggest blocks women hit going from six figures to seven figures
31:00 – Visibility, people-pleasing, and identity shifts in business growth
36:00 – Why most successful businesses focus on beginners
41:00 – The simple seven-figure business model (and why it’s simpler than you think)
47:00 – Improving messaging and positioning for entrepreneurs

Links Mentioned in This Episode
https://forthe23percent.com/
Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, March 13)

Watch & Listen
Watch this episode on YouTube and listen on all podcast platforms:
Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
YouTube: https://www.youtube.com/sidehustlepro

Announcements
If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class:: Start the Podcast That Builds Your Exit Plan
Save your seat here:

Social Media
Instagram: @forthe23percent
Side Hustle Pro – @sidehustlepro
#SideHustlePro
Hosted on Acast. See acast.com/privacy for more information.