The Scaling Podcast With Aaron Harper

Scarlett shares her journey from Deloitte and L'Oréal to launching multiple startups, including her latest venture Pretty Tasty. This conversation dives deep into the realities of fundraising, choosing the right investors, and why patient capital often beats private equity timelines. Entrepreneurs will hear tactical lessons on scaling, risk, and building businesses that last. Intro & premise — 00:00:00:00–00:00:31:00 Founder & company intro (Pretty Tasty) — 00:00:31:02–00:01:06:18 Career background: Deloitte → Philip Morris → L'Oréal → AllSaints → FreshDirect — 00:01:06:20–00:03:01:19 First startups: egg freezing clinic → Sugar Break (venture-backed) & lessons — 00:03:01:21–00:03:57:21 Capital philosophy: family office backing, investor belief, flexibility vs. PE timelines — 00:03:57:23–00:05:26:21 Beverage model realities: capital intensity, scarce acquirers, ops co-founders — 00:05:26:21–00:07:22:21 Play to strengths + fundraising approach (strategic raises, no pressure to VC ladder) — 00:07:22:23–00:09:06:17 Product thesis & origin: collagen iced tea, authenticity, food-as-medicine roots — 00:09:06:17–00:10:47:11 Formulation & launch: zero sugar, stevia tuning, Expo West, 'Best New Beverage' — 00:10:47:13–00:12:55:14 Distribution mechanics: 2 major distributors, buyer sell-in, stocking dynamics — 00:13:21:06–00:14:40:14 Retail rollouts & door count (CVS, Sprouts, West Coast, NYC; ~2,000 doors) — 00:14:40:14–00:16:03:02 Founder-led sales & relationships (store tours, end caps, signage, sampling) — 00:16:03:02–00:17:11:08 Scale path vs. Poppy; margins reality; iterate fast on-market — 00:17:34:22–00:20:12:18 Packaging & messaging iteration (readability, flavor color, 'daily collagen', 10g protein) — 00:19:40:03–00:22:12:18 Marketing & education: social, local influencers, retail activations, Sephora demos — 00:23:58:15–00:26:32:08 DTC vs. retail models: AG1, Starbucks placement, Costco for awareness; when to add big influencers — 00:26:32:08–00:30:12:09 Operator lessons: 'fail fast'; in-person sampling beats surveys — 00:32:30:15–00:34:38:21 Scaling life: systems at home, childcare help, energy tradeoffs — 00:39:56:08–00:41:13:11 Support network, rest habits, cooking & crafts, meditation — 00:41:13:11–00:44:24:22 Team plan: shared resources now → build in-house marketing/community — 00:44:24:22–00:45:20:09 Exit route & timeframe (sell to strategic; 5–10 years) — 00:45:43:04–00:46:31:20 Hiring a CEO; resource allocation as top CEO trait; founder identity shift — 00:46:31:22–00:57:30:13 Franchising & international: Middle East/LATAM partners; legal complexity; negotiation & cultural fit — 00:59:27:20–01:05:13:17 Closing founder advice: it's hard/lonely; know your 'why'; grit; swing big — 01:05:57:20–01:07:29:09 Outro & where to find — 01:07:29:11–01:07:52:11

Michael Zuber thought financial freedom would be the finish line. At 45, with 170+ rental units, he had it all—except purpose. In this episode, Aaron and Michael unpack the transition from corporate life to entrepreneurship, the surprising challenges of "making it," and the disciplines that sustain both health and business success. Whether you're an entrepreneur scaling up, or someone chasing financial independence, Michael's story is a reminder: freedom is only the beginning.

In this episode, Aaron Harper sits down with Andrew — a longtime friend and business leader — to talk about 20 years of friendship, the realities of raising capital, and what it really takes to build something meaningful. We cover stories from college dorm rooms to navigating sharks in the world of venture capital. Whether you're interested in franchising, entrepreneurship, or just a real conversation about growth, this episode has it all. 00:00 - 00:01:17 | Introduction Aaron introduces Andrew, their 20-year friendship, and Andrew's role as an advisor in Rolling Suds. 00:01:17 - 00:08:39 | College Days & Dorm Room Stories Meeting at 18, clashing as roommates, transferring to UCSB, living in Isla Vista, and balancing work with nonstop parties. 00:08:39 - 00:12:07 | Building a Lasting Friendship Why their bond has lasted: differences that complement each other, honesty, and growing through different life stages. 00:12:07 - 00:15:54 | Early Signs of Leadership Aaron's ability to rally people, the Santa Barbara Digital Film Festival, and lessons from executing big visions young. 00:15:54 - 00:20:47 | Reconnecting After Hard Times The fallout during Aaron's darker years, rebuilding their friendship in 2018, meeting Sarah, and opening a new chapter of life. 00:20:47 - 00:25:12 | From Employee to Entrepreneur Aaron's shift from top franchise salesperson to pursuing his own business, influenced partly by Alex Hormozi. 00:25:12 - 00:34:20 | Raising Capital & Taking the Leap Losing his job, burning the boats, and navigating sharks in the water while raising money. 00:34:20 - 00:40:06 | Learning Fast & Building Support Systems Crash course in deal structures, protecting ownership, and leaning on trusted advisors. 00:40:06 - 00:44:50 | The Value of Honest Feedback Why Andrew chose not to invest or join as co-founder, instead offering outside perspective. 00:44:50 - 00:49:42 | Scaling Rolling Suds Aaron's leadership, startup culture vs franchising, and loneliness in entrepreneurship. 00:49:42 - 00:54:10 | Friendship & Family in Business How honesty, trust, and shared values shape both family life and business growth. 00:54:10 - End | Lessons Learned & The Road Ahead Reflections on 20 years of friendship, building something bigger than yourself, and what's next.

Shaina Denny, founder of Dog Drop, shares her journey in creating a tech-enabled dog daycare that thrives on convenience and community. She discusses the key challenges in scaling a franchise, emphasizing the importance of in-house technology and strong franchisor–franchisee partnerships. Shaina offers insights into member acquisition through multifamily partnerships and explains her unique fundraising approach. She also highlights the value of authenticity in marketing and the necessity of a measured growth plan to ensure lasting success.

Aaron Harper sits down with Kelcey Lehrich, co-founder of 365 Holdings, to unpack how he and his partner built a portfolio of consumer brands doing $60M+ in revenue—without raising outside capital. From buying a business with a $10K down payment to navigating a near financial meltdown in 2023, this episode is packed with hard-earned wisdom on e-commerce, partnerships, and founder resilience. ⏱️ Timestamps & Topics: 00:01 – Making friends in your 30s through business, skiing, and Twitter 01:09 – Kelcey's first ecommerce business and how 365 Holdings began 02:53 – Scaling from $2M to $60M in revenue 04:30 – How many brands are in the portfolio (and how many flopped) 05:51 – The original thesis vs. today's strategy 06:45 – Why the e-commerce aggregator model failed (Thrasio, etc.) 09:00 – Starbucks vs. "duct-taped" coffee shops analogy 10:30 – Kelcey's favorite type of business: own supply AND demand 11:20 – Cuddle Clones: the artisan product business they scaled 12:40 – Community, connection, and why Kelcey joined YPO 14:50 – The jump from $45M to $60M: acquisition + turnaround 16:40 – Buying a distressed jewelry brand (Brian Anthony's) 17:44 – Tariffs, China, and global supply chain strategy 20:14 – Kelcey's role: M&A, external relationships, and deal flow 21:19 – Ideal acquisition pace: 1 every 9 months 22:22 – "SEAL Team" for turnarounds + special situations 23:08 – Why they love distressed deals over premium growth buys 24:21 – What's happening in capital markets & Holdco land 25:52 – No outside capital: how they bootstrapped from $10K 27:17 – 2023 financial crisis: the CFO lied, debt stacked up 30:00 – Daily cash flow, layoffs, workouts… and recovery 32:39 – How Kelcey's wife handled the meltdown at home 34:56 – Faith, identity, and separating self-worth from business 37:30 – Aaron's personal story: baby on the way, stepping back, hiring a CEO 40:24 – "I'm not my business" → writing it all down → reset 41:43 – Growth curve pressure: why some team members can't keep up 43:00 – Making space for others to rise as the founder steps back 45:43 – Ironman idea: Aaron's next personal growth & content move 46:14 – Kelcey gave up his office to make room for the CFO 47:38 – Holding company evolution: ops vs. strategic layer 50:12 – Kelcey on content: "not a focus, but I'll show up if it's meaningful" 52:59 – Why he shares: paying it forward to the next entrepreneur 54:45 – How Aaron's Twitter & podcast directly drove revenue and talent 56:25 – Kelcey's soapbox: "There is no such thing as an e-commerce business" 59:00 – The danger of launching too many brands in a holdco 01:00:54 – "Your worst asset is always for sale" – capital allocation logic 01:02:14 – Why Aaron isn't opening trucks—his CEO is on a listening tour 01:04:01 – What comes next as Rolling Suds scales

Thinking about buying a business? Not sure what's real and what's hype? In this episode of The Scaling Podcast, Aaron Harper sits down with Matthias Smith, founder of Pioneer Capital, to unpack exactly how SBA financing works, what makes a business lendable, and the harsh truths nobody on TikTok is telling you. From seller equity to working capital to divorce derailing deals (seriously), this episode dives deep into the real mechanics of acquisitions — whether you're a searcher, operator, or future franchisee. Timestamps: 0:00 Intro 3:00 How Matthias helps business buyers get financed 6:50 Where deal flow comes from 10:00 SBA myths (zero money down?) 14:00 Seller equity changes 20:00 Why some businesses can't be sold 25:30 Real talk on finding deals 35:00 Real estate in SBA loans 47:00 Bigger deals & private equity pressure 55:00 Aaron's origin story 1:02:00 Why capital matters when starting Learn more about Matthias: Website: https://pioneercap.com X (Twitter): @SBA_Matthias

Tariq Johnson, an entrepreneur and former multi-unit franchisee, shares his valuable insights on franchising. He unpacks the stark realities of investing in franchises, highlighting common pitfalls and mismatched expectations. Tariq discusses his personal journey through eight failed businesses and how franchising became his path to success. He emphasizes the importance of education and support for franchise buyers. Listeners will discover why some franchisees thrive while others struggle, and the critical questions aspiring owners should ask before diving in.

In this episode, Aaron Harper sits down with Eric Pacifici—attorney, entrepreneur, and co-founder of SMB Law Group—to discuss what every franchise buyer, founder, and seller needs to know about small business transactions, legal pitfalls, and structuring deals the right way. From leaving Big Law to closing over $1B in Main Street transactions, Eric shares hard-earned lessons on legal innovation, franchise diligence, and how social media unexpectedly launched one of the most trusted firms in SMB M&A. 00:00 – Intro 01:41 – Eric returns and shares his backstory 03:30 – Why he left Big Law and redefined success 05:10 – Founding SMB Law Group and identifying unmet legal needs 07:30 – The problems with billable hours and deal structures 10:12 – Tradeoffs of innovating in a traditional industry 12:41 – Launching a law firm off a Twitter account 14:00 – Early traction, demand problems, and scaling the team 16:30 – What makes a "blue chip ETA" deal work 17:50 – Building the Kirkland & Ellis of Main Street 19:45 – Remote-first legal practice and quality of life 21:00 – Golden handcuffs, entrepreneurship, and personal freedom 25:30 – Franchising overlap: why M&A and franchise law intersect 27:00 – Franchise diligence and risks 28:30 – Trends in ETA and franchise buyers 30:45 – SBA 7(a) deal structures explained 34:50 – Silver tsunami, generational wealth transfer 39:30 – How to structure "ugly" or non-underwritable deals 42:00 – Earn-outs, seller financing, and legal risk mitigation 45:25 – Franchising through acquisition strategy 47:24 – Legal marketing and firm visibility 48:41 – Where SMB Law gets its clients: Twitter, referrals, and more 52:07 – The value of project-based legal work 54:16 – Marketing restrictions for lawyers + content strategy 56:14 – Why Eric started creating content accidentally 57:30 – Social media and personal brand dynamics 59:30 – Commentary on content creators and public perception 01:07:29 – Lessons from Alex Hormozi and the value of free education 01:09:40 – How social media influences franchise client growth 01:11:46 – Feedback, self-awareness, and creating authentic content 01:13:00 – Final thoughts on building a business with soul

In this episode of The Scaling Podcast, Aaron Harper sits down with Collin Rutherford—founder of two fully remote businesses: Greenbox Storage and Founder Brands. They dive deep into what it actually takes to scale a startup without an office, how to lead through chaos, and why your business only grows as much as you do. 00:00 – Intro Aaron introduces Collin and sets up the episode 01:15 – Launching Greenbox Storage in College How Collin started the business as a junior at Dartmouth 02:59 – Transitioning to Remote Operations From driving U-Hauls to running 23 campuses remotely 04:40 – Customer Acquisition with Email & Interns Email marketing + boots-on-the-ground interns = growth strategy 08:27 – Starting Founder Brands How building his own content system led to a new business 10:08 – The Monthly Content Framework One recording → a full month of written + video content 12:34 – Case Study: Local Hockey Coach → Newsletter & YouTube How content transformed a small business's growth 13:59 – Letting Go of Daily Ops Why Greenbox runs without Collin today—and how he got there 16:38 – Founder Brands: Still in the Trenches Finding product-market fit and building an A+ team 18:12 – Founder's Role in Early-Stage Growth Lead gen, sales, and how founders should spend their time 20:10 – Going All-In on Twitter (X) Why June 2023 was Collin's turning point for personal branding 21:43 – Stop Posting. Start Engaging. How to grow from 100 followers to 1,000+ by leveraging others' reach 27:50 – Lead Magnets & Email Growth The power of gated value and building a subscriber list 32:13 – Aaron's Content Flywheel at Rolling Suds Using content to replace a sales role and scale franchise leads 33:18 – Stories Always Win Why personal stories outperform tips in tough algorithm cycles 34:34 – Social as Leverage (Not Just for Leads) Use your brand to hire, raise money, and build your network 35:45 – Followers Are a Vanity Metric Real revenue from small audiences and niche accounts 37:56 – Tribe: Founder Peer Group Benefits How Collin finds support, connection, and perspective 42:00 – Bringing On a Co-Founder Why Collin sold 20% of his company and how he structured the deal 44:38 – First Acquisition: Buying a Competitor How a helpful email turned into an M&A deal 46:54 – Greenbox's Ceiling & Growth Strategy How big this niche business can get—and what it takes to get there 48:53 – What Collin Needs to Grow Next Founder evolution, systems, and recruiting the right people 54:47 – Quick Interruption (Cleaners) Aaron returns to continue the deep dive 55:38 – Partner's Role and Work-Life Balance Collin shares what his girlfriend does and how they live remotely 56:00 – Why Entrepreneurship Freedom, flexibility, and risk vs reward 57:26 – The Hard Part: No One Tells You What to Do Entrepreneurship means making decisions in the dark 58:14 – $20K Mistake: Auctioned Storage Units The hardest calls Collin ever had to make—and how he recovered 01:03:28 – Advice for First-Time Founders Solve a real problem. Don't reinvent the wheel. 01:09:25 – Why One Business is Usually Enough Walker Deibel's advice on focus vs fragmentation 01:13:08 – Final Thoughts on Growth & Discipline What to do when you already have something working

Scott Abbott, a serial entrepreneur and franchise guru, shares his journey from launching his first business at 15 to scaling Five Star Painting into a franchise with 1,500+ locations. He discusses the critical lessons learned from a failed partnership and the importance of marketing strategies like A/B testing. Scott delves into the 'feed what works' philosophy for growth, highlights the significance of building systems independent of founders, and emphasizes the value of integrating family and work. He also shares insights on partnerships and plans to acquire more brands in the future.