Most founders avoid this question until it's too late: Should you still be the CEO of your own company?

Mackie Swan was brought in by the three original founders of WOO More Play—a sexual wellness brand sold in Anthropologie, Nordstrom, and Revolve—to scale a business they realized they shouldn't be running day-to-day. Three years later, she's taken the business to profitability while navigating the complex world of "vice categories."

This isn't a conversation about sexual wellness products. It's about a decision many founders will eventually face: Am I the right person to be running the company I founded?

In this episode, we explore:
The "Capacity vs. Desire" framework: How to know if you've outgrown the CEO role
What the transition process actually looks like when bringing in an outside CEO
How to structure compensation and equity to align incentives
Why procrastination might be telling you you're in the wrong role
How to hire people who will actually tell you when you're wrong
What "vice categories" means and the hidden operational challenges (PayPal froze $50K+ of their funds overnight)
Why Mackie tracks EBITDA daily instead of typical vanity metrics
The difference between being a founder and being a CEO—and why they're not the same thing

Whether you're a founder questioning your role, considering bringing in outside leadership, or an operator thinking about joining an early-stage brand, this conversation offers rare insight into a transition most founders don't talk about until it's too late.

Guest Links:
WOO More Play: woomoreplay.com
Instagram: @woomoreplay
LinkedIn: Mackie Swan

I hope you enjoyed this episode!
Give it a like, share, and subscribe to not miss the content coming your way weekly.
– Nate and the Profits on Purpose podcast team

Connect with Nathan Littlewood on LinkedIn: https://www.linkedin.com/in/nathanlittlewood/
Visit the Future Ready CFO website here: https://www.futurereadycfo.com/
Join the Future Ready Newsletter here: https://www.futurereadycfo.com/newsletter

Listen to Profits on Purpose on these podcast platforms:
Spotify: https://open.spotify.com/show/1h3U1cG0zhaSwqa8f2UFXI
Apple Podcasts: https://podcasts.apple.com/us/podcast/profits-on-purpose/id1826982087
Amazon Podcasts: https://podcasts.apple.com/us/podcast/profits-on-purpose/id1826982087

#profitsonpurpose #nathanlittlewood #futurereadycfo #financeleadership #cfoinsights #purposeledbusiness #scalingforimpact #financialstrategy #purposeledprofit #missiondrivengrowth #sustainablebusiness #businessleaders #entrepreneurmindset #financialclarity #scalingbusinesses #ethicalentrepreneurship #businessstrategy #impactfulleadership #cforole #executivethinking
Welcome to the Profits on Purpose podcast, where we explore the journeys of purpose-led founders and the financial strategies that help them survive and thrive. Host Nate Littlewood sits down with eCommerce and CPG founders to unpack the real-life tension between a brand's mission and the practical realities of generating profit.

In this episode of Profits on Purpose, host Nate Littlewood sits down with Tapasya Bali, a rare entrepreneur who speaks both Wall Street and Main Street. After 16 years navigating high-stakes finance at Credit Suisse, Tapasya made a bold pivot at the peak of her career to co-found Yogasmoga, an athletic apparel brand that scaled to a $74 million valuation and earned her recognition as one of Goldman Sachs's 100 most intriguing entrepreneurs.

Today, she's building 100 Cal Snacks, a functional food brand tackling the healthy snacking space with laser-focused positioning around the gut-brain connection. Through her consulting business, My Consumer Brand, she helps founders navigate the intersection where brand storytelling meets financial sustainability.

This conversation dives deep into the quantitative approach to brand positioning, the critical difference between market trends and patterns, and why most founders get the timing wrong on both branding investments and financial planning. Tapasya shares hard-won lessons about building teams, managing investor expectations, and why your spreadsheet projections matter more for the logic they reveal than the numbers themselves.

If you've ever wondered how to find white space in crowded markets, when to implement give-back initiatives without destroying margins, or how to tell your company's story in financial terms that investors actually want to hear, this conversation delivers.

KEY INSIGHTS:

Brand positioning is fundamentally quantitative. Before the storytelling comes deep market research, competitor mapping, and data validation to find genuine white space in crowded categories.

Distinguish between trends and patterns. Trends die quickly, but patterns reveal lasting consumer pain points. Gut health was trending, but the gut-brain connection represents a pattern with staying power.

Your financial projections are planning tools, not predictions. The value isn't in hitting exact numbers but in forcing yourself to articulate your go-to-market strategy and the logic behind your growth assumptions.

Invest in brand positioning before brand design. Most founders skip the strategic foundation and jump straight to logos and color schemes, then struggle with diluted messaging that doesn't differentiate.

Marketing Efficiency Ratio matters more as you scale. While margins are table stakes, MER determines your ability to deploy capital effectively and directly impacts exit valuations and EBITDA multiples.

Give-back initiatives can destroy value if poorly timed. Unless structured as self-sustaining models, charitable components eat into bottom lines and compress valuations that investors care about.

The transition from finance to entrepreneurship is humbling. Even working 12-hour days on a trading desk doesn't prepare you for the sheer breadth of skills and relentless execution required to build a consumer brand.

Patience is the hardest skill for high-velocity professionals. Consumer businesses move slower than finance. Retail timelines, fundraising cycles, and shelf placement all require recalibrating expectations from Wall Street pace.

CONNECT WITH TAPASYA:

LinkedIn: https://www.linkedin.com/in/tapasya-bali/
100 Cal Snacks: 100calsnacks.com
My Consumer Brand: myconsumerbrand.com

If this episode helped you think differently about brand positioning or financial strategy, share it with a founder who needs to hear it.

I hope you enjoyed this episode!
Give it a like, share, and subscribe to not miss the content coming your way weekly.
– Nate and the Profits on Purpose podcast team

Connect with Nathan Littlewood on LinkedIn: https://www.linkedin.com/in/nathanlittlewood/
Visit the Future Ready CFO website here: https://www.futurereadycfo.com/
Join the Future Ready Newsletter here: https://www.futurereadycfo.com/newsletter

Listen to Profits on Purpose on these podcast platforms:
Spotify: https://open.spotify.com/show/1h3U1cG0zhaSwqa8f2UFXI
Apple Podcasts: https://podcasts.apple.com/us/podcast/profits-on-purpose/id1826982087
Amazon Podcasts: https://podcasts.apple.com/us/podcast/profits-on-purpose/id1826982087

#profitsonpurpose #nathanlittlewood #futurereadycfo #financeleadership #cfoinsights #purposeledbusiness #scalingforimpact #financialstrategy #purposeledprofit #missiondrivengrowth #sustainablebusiness #businessleaders #entrepreneurmindset #financialclarity #scalingbusinesses #ethicalentrepreneurship #businessstrategy #impactfulleadership #cforole #executivethinking
Welcome to the Profits on Purpose podcast, where we explore the journeys of purpose-led founders and the financial strategies that help them survive and thrive. Host Nate Littlewood sits down with eCommerce and CPG founders to unpack the real-life tension between a brand's mission and the practical realities of generating profit.

In this episode of Profits On Purpose, host Nate Littlewood speaks with Bellamy Grindl, founder of Retailytics, about the intricacies of inventory management and supply chain operations for e-commerce and CPG founders. They discuss the evolution of operations as businesses grow, common inventory challenges, the importance of breaking down silos between departments, and strategies for effective planning and communication. Bellamy shares insights on navigating post-holiday sales recovery, the impact of COVID on supply chain strategies, and the significance of financial literacy and technology in managing inventory effectively. The conversation concludes with key performance indicators and resources for further learning.

Connect with Bellamy:
LinkedIn: https://www.linkedin.com/in/bellamygrindl/
Instagram: https://www.instagram.com/retail_ytics/
YouTube: https://www.youtube.com/@retail_ytics
Official Website (URL): www.retailytics.co

I hope you enjoy this episode!
Give it a like, share, and subscribe to not miss the content coming your way weekly.
– Nate and the Profits on Purpose podcast team

Connect with Nathan Littlewood on LinkedIn: https://www.linkedin.com/in/nathanlittlewood/
Visit the Future Ready CFO website here: https://www.futurereadycfo.com/
Join the Future Ready Newsletter here: https://www.futurereadycfo.com/newsletter

Listen to Profits on Purpose on these podcast platforms:
Spotify: https://open.spotify.com/show/1h3U1cG0zhaSwqa8f2UFXI
Apple Podcasts: https://podcasts.apple.com/us/podcast/profits-on-purpose/id1826982087
Amazon Podcasts: https://podcasts.apple.com/us/podcast/profits-on-purpose/id1826982087

#profitsonpurpose #nathanlittlewood #futurereadycfo #financeleadership #cfoinsights #purposeledbusiness #scalingforimpact #financialstrategy #purposeledprofit #missiondrivengrowth #sustainablebusiness #businessleaders #entrepreneurmindset #financialclarity #scalingbusinesses #ethicalentrepreneurship #businessstrategy #impactfulleadership #cforole #executivethinking
Welcome to the Profits on Purpose podcast, where we explore the journeys of purpose-led founders and the financial strategies that help them survive and thrive. Host Nate Littlewood sits down with eCommerce and CPG founders to unpack the real-life tension between a brand's mission and the practical realities of generating profit.
Each episode digs into the leadership insights and financial approaches that empower consumer products businesses to grow with clarity, resilience, and impact. You'll get a behind-the-scenes look at how visionary founders reconcile their purpose with the everyday demands of scaling a successful brand and leading with both mission and margin.
If you're a founder, finance leader, or simply navigating the purpose-profit paradox, this podcast is for you.