Side Hustle Pro

This week in the guest chair is Leah Collins, financial coach, speaker, and host of Maxxed Out, a powerful series helping people confront their finances and the relationships tied to them. But Leah’s journey didn’t start on TV, it started with a moment of truth: making the most money she ever had… and realizing she had nothing to show for it.

In this episode, I sit down with Leah to unpack how she transformed her own financial struggles into a thriving business, paid off $40,000 in debt, and ultimately landed her own show. We talk about the behind-the-scenes reality of building a personal brand, why communication is the foundation of financial success, and how she leveraged every opportunity to create multiple income streams.

Leah also opens up about one of the most pivotal moments in her life: calling off her wedding due to financial incompatibility. That experience reshaped her entire mission and led her to focus on money and relationships, helping others navigate the conversations so many of us avoid. This episode is a masterclass in turning pain into purpose and building a life that aligns with your values.

Main Takeaways
Turning personal financial struggles into a business can create powerful impact and income
Financial compatibility and communication are critical in relationships
Your personal brand is always working for you, even when you don’t realize it
Multiple income streams, including speaking, media, and passive products, create flexibility and freedom

Highlights Include
00:00 – Why money affects every part of your life
02:10 – 20 years in corporate finance but struggling personally
04:05 – Wake-up call: high income, no results
04:40 – $100 bootcamp → $40K debt paid off
05:20 – Calling off her wedding over money misalignment
07:06 – Prenups, communication, and financial expectations
09:05 – Turning personal pain into a business niche
10:53 – Launching her brand → getting discovered for TV
12:11 – Building a strategic personal brand that attracts opportunities
14:17 – TV journey: rejection, delay, and eventual greenlight
16:46 – Scaling after motherhood and shifting business model
20:43 – Behind the scenes of Maxed Out and building trust
23:03 – Leveraging TV into multiple income streams
24:55 – Values-based finances and smarter decision-making
26:51 – Balancing a 9–5 while growing a business
29:37 – Storytelling as a tool for impact and connection
31:27 – Pitching yourself and understanding media monetization
34:11 – “You’re always being interviewed” mindset
38:13 – Why quality beats quantity in content
41:02 – Burnout, boundaries, and protecting your time
41:42 – Final advice: build your business without quitting your job

Links Mentioned in This Episode
Money Moves Makeover: https://www.amazon.com/
OWN Network: https://www.oprah.com/own
HBO Max: https://www.max.com/
Discovery+: https://www.discoveryplus.com/
Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, May 15)

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:@theleahmariecollins

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

I sat down with Monica Cornitcher, CEO and co-founder of Medase Cocktails, a premium non-alcoholic beverage brand redefining what it means to drink without alcohol. What started as a simple desire for a real cocktail experience without the after-effects turned into a six-figure investment and a fast-growing brand that’s now catching the attention of major retailers.

Monica shares how she and her co-founder Inga Dyer went from Zoom conversations during the pandemic to building a fully developed beverage company. Instead of rushing the process, they leaned into research, worked with a food scientist, and built a five-year strategy before launching. Their focus was clear: create authentic, full-flavor cocktails that people actually recognize and crave.

In this episode, Monica opens up about the real cost of building a physical product, navigating grief after losing her co-founder, and the strategy behind growing through direct-to-consumer before entering retail. This is a powerful conversation about resilience, intentional growth, and building a brand rooted in purpose and community.

Main Takeaways
Why taking time to validate your idea and build a strategy can save you costly mistakes
How to approach launching a physical product without cutting corners on quality
The importance of direct-to-consumer growth before entering retail
How resilience, grief, and purpose shaped the future of Medase Cocktails

Highlights Include
00:00 – Introduction to Medase Cocktails
03:00 – Monica’s first business and corporate background
06:00 – The idea sparked during COVID and building with intention
08:00 – Why they worked with a food scientist instead of DIY
10:00 – Creating a 5-year business strategy before launch
13:00 – Identifying their target consumer and product positioning
21:00 – Funding the business with $100K+ of personal investment
26:00 – Attending Expo West and attracting investors
29:00 – Navigating grief after losing her co-founder
30:00 – Growth on Amazon and direct-to-consumer success
33:00 – Why retail is expensive and how to prepare for it
45:00 – Lessons from production mistakes and product quality control
47:00 – Competing in a growing non-alcoholic beverage market
50:00 – Lightning round insights and tools

Links Mentioned in This Episode
Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, May 15)

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: @medasecocktails
TikTok: @medasecocktails
Facebook: Medase Cocktails

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

In this episode, I’m joined again by Monique Shields, and this conversation felt like therapy, coaching, and truth-telling all in one. We went deep into something I’ve personally been navigating: what it actually looks like to move out of survival mode as a high-achieving woman, especially when life has been life-ing.

We talked about the invisible weight many of us carry, from parenting to business to unexpected life challenges, and how that impacts the way we show up, make decisions, and even spend money. One of the biggest shifts for me? Realizing I wasn’t telling myself the full story about what I had been carrying and surviving.

Monique breaks down how our mindset around scarcity, energy, and outsourcing can keep us stuck, and what it really means to “resource yourself” instead of just pushing through. If you’ve been feeling stuck, foggy, or like you’re doing everything but still not moving forward, this episode will hit home.

Main Takeaways
You’re not behind, you’re likely operating without acknowledging everything you’ve been carrying
Scarcity mindset after a hard season can quietly shape your decisions and keep you stuck
Your energy, not just your time, is one of your most valuable assets
Resourcing yourself (mentally, physically, strategically) is essential for growth

Highlights Include
00:00 – Reconnecting with Monique and what she’s been building
02:30 – Why intimate spaces and coaching containers matter
04:30 – Starting YouTube and breaking through creative burnout
06:00 – The hidden impact of hard seasons on decision-making
08:00 – Why you’re not telling yourself the full story
10:00 – High-achievers and the trap of self-pressure
12:30 – Why “feeling less overwhelmed” isn’t the right goal
15:00 – Scarcity mindset after financial or life shocks
18:00 – Why cost-first thinking keeps you stuck
21:00 – The “delusional belief” successful people hold about their future
27:00 – The real value of your time and energy
33:30 – What actually changed after hiring support
36:00 – Mental fog and why you don’t even realize you’re in it
40:00 – Why stability is not the same as hoarding
43:00 – What it really means to “resource yourself”
46:00 – The importance of having multiple “brains” supporting you
50:00 – Why your nervous system needs support in today’s world
52:00 – Reframing “I can’t afford it” into a choice

Links Mentioned in This Episode
Save the Date: Start the Podcast That Builds Your Exit Plan (April 17)

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: @moniquershields
Podcast: Ambition Without Compromise

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

This episode is one of the most personal and vulnerable conversations I’ve ever shared. I’m opening up about my journey as an autism mom, from the early days of pregnancy and motherhood during the pandemic to navigating the realities of developmental delays, diagnoses, and advocacy.

What started as subtle concerns about speech delays turned into a life-changing journey through early intervention, therapy, and eventually receiving an official autism diagnosis for my son. Along the way, I’ve had to learn how to advocate fiercely, navigate complex systems, and redefine what motherhood looks like for me and my family.

This episode is about the hard moments, the emotional weight, and the unexpected beauty in this journey. It’s also about community, resilience, and learning to see strength in a path that looks different than what I once imagined.

Highlights Include
00:00 – Why this episode is deeply personal
02:00 – Pregnancy, birth, and early milestones during the pandemic
04:30 – First signs of speech delay and comparing developmental milestones
06:30 – The emotional impact of early evaluations
07:30 – Starting early intervention: speech and occupational therapy
09:00 – Transition to specialized preschool and navigating the system
11:00 – The hidden challenges of parenting a child with special needs
12:30 – Communication barriers and emotional regulation as a parent
14:00 – The moment I realized how much I’ve been carrying
16:40 – Understanding gestalt language processing
19:30 – Getting an official autism diagnosis
21:00 – Advocating for my son within the school system
23:30 – A “guardian angel” moment that changed everything
27:00 – The role of faith in navigating this journey
29:00 – Finding community and learning from other moms
30:30 – Lessons autism has taught me about boundaries and perspective
31:00 – A real-life parenting moment at the barbershop
33:00 – Choosing celebration during Autism Awareness Month

Links Mentioned in This Episode
• Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 17)

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.

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.