The Deal Closers Podcast

Hosted by Website Closers

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Sep 2025

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About the show

Welcome to The Deal Closers Podcast - a show about how to build your ecommerce business to be profitable, scalable, and one day, even sellable. Hosted by the team at WebsiteClosers.com, and produced by Walk West. Hosted on Acast. See acast.com/privacy for more information.

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September 9, 202546 min

Building a $40M Global Brand as a Digital Nomad, with Dan Demsky

What does it look like to build a seven-figure business by accident and then use those lessons to build a $40 million company on purpose? Meet Dan Demsky, CEO of Unbound Merino. After building a successful service agency that left him feeling like a prisoner, Dan started over with a new vision - to create a profitable, scalable business that truly supported his freedom and lifestyle. In this episode, you’ll hear how he used a smart crowdfunding strategy, obsessed over product quality, and built a successful company with his best friends - all while working from wherever he wanted. In this episode: The key differences between a "service-based" and a "product-based" business model How to use a crowdfunding campaign to validate an idea, raise capital, and find your first 2,000 customers The "manufactured momentum" strategy that helped Unbound Merino exceed its funding goal by over 1,000% Why working with your best friends can be the best business decision you'll ever make How to build a profitable, multimillion-dollar brand without high overhead, a massive team, or an office Why obsessive product quality is the ultimate marketing strategy for a direct-to-consumer brand Timestamps 00:01:42 – From a childhood snow-shoveling hustle to a seven-figure agency 00:06:05 – The shift from a service business to a product-based brand 00:08:15 – The "Aha!" moment that led to Unbound Merino 00:14:40 – A breakdown of the wildly successful crowdfunding strategy 00:21:00 – The biggest challenges and lessons from early fulfillment 00:24:20 – Why Dan believes working with your best friends is an amazing way to live 00:34:50 – The surprising strategy behind building a lean, efficient company 00:38:00 – The philosophy of a "lifestyle business" and its benefits 00:43:00 – Why obsessing over product quality is the best marketing This episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West. Hosted on Acast. See acast.com/privacy for more information.

August 19, 202537 min

How Michael Haase Built and Sold Quantix (with Website Closers' Help)

What does it look like to prepare a company for sale when you've just bought it? And what do buyers really care about when they’re looking to acquire? That’s what Michael Haase and his brother, through their firm Think Global, do. And after preparing countless businesses for acquisition, they had the opportunity to put their own advice into practice when they bought - and then recently sold (with Website Closers' help) - the tech staffing company Quantix. In this episode, you’ll learn: How to grow a tech business by focusing on quality and deep relationships instead of competing on price The difference between running a business and "purpose-building" it for a future exit Why it’s crucial to have your financials and data room in order long before you decide to sell The importance of working with a broker you trust to vet buyers and navigate a complex, emotional process How one deal broke—and how having the right team in place saved the sale What buyers look for in a company, from its operational health to its team culture Timestamps 00:01:40 – From Air Force tech to seasoned entrepreneur 00:03:52 – Starting his first company and taking the leap 00:06:58 – The decision to buy a business with his brother 00:08:00 – Helping other founders prepare for an acquisition 00:18:00 – Why Michael decided to use a broker 00:19:30 – How a broken deal almost ended the sale 00:22:20 – Why Michael’s team was his first priority during the sale 00:32:15 – What made QuantX so attractive to buyers 00:34:00 – How Michael and his brother celebrated the sale 00:35:20 – How to connect with Michael and Eric This episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West. Hosted on Acast. See acast.com/privacy for more information.

August 5, 202540 min

From Devastating Hacks to a Successful Exit: Skivys Femme's Kelly Degnan

From a childhood business selling painted buckeyes to a multi-million dollar loungewear brand, Kelly Degnan has always been a creative entrepreneur. She built Skivys Femme from a simple idea during the pandemic into a seven-figure success story, only to face a domain hack and an inventory crisis that threatened to derail it all. In this episode, Kelly shares her rollercoaster journey, from bootstrapping her first business to making the tough decision to sell—even when her books weren't at their peak. You’ll learn: How a simple problem during the pandemic turned into a seven-figure business The pros and cons of bootstrapping your brand to millions in revenue The devastating impact of a domain hack and how to protect your business Why "off-peak" sales seasons can present the biggest challenges How to find the right broker who will be a "therapist" through the emotional journey of selling The surprising benefits of a fast sale with a strategic buyer The joy of staying on with the new company and focusing only on the work you love Timestamps: 00:01:00 – From a childhood side hustle to launching Skivys Femme 00:05:41 – Bootstrapping and finding the perfect overseas manufacturer 00:10:00 – How ad agencies and then a single expert helped drive massive growth 00:15:20 – The "Oh crap" moment: a domain hack and inventory crisis 00:20:41 – Why Kelly started exploring an exit 00:23:05 – Eric Pittman's initial advice on selling and when the timing is right 00:27:00 – The benefits of selling to a strategic buyer 00:28:03 – Staying on and focusing on the roles you love 00:29:19 – Kelly's advice for other business owners thinking about an exit 00:32:41 – Introducing her new brand, Vital Youth Blends (Vibe) 00:37:34 – How Kelly celebrated the sale with her son For 30% off from Kelly's new product, go to https://www.vitalyouthblends.com/ and use promo code VIBE30. This episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West. Hosted on Acast. See acast.com/privacy for more information.

July 22, 202530 min

Evaluating Risk and Reward when Buying Companies, with Mahati Sridhar

If you're thinking about investing beyond the stock market, where do you even begin? What does it truly take to identify promising companies and founders? In this episode of Deal Closers, host Jason Gillikin welcomes Mahati Sridhar, Partner at Revolution's Rise of the Rest Seed Fund. With extensive experience in the venture capital ecosystem, Mahati shares invaluable insights for both aspiring angel investors and those looking to acquire an entire business. She reveals the critical factors VCs consider, common investor mistakes, and how to navigate the complexities of M&A from the buyer's perspective. You’ll learn: The key differences in evaluation criteria for angel investors vs. VCs Why investing in early-stage companies is fundamentally about investing in people How to build genuine relationships with founders to assess their resilience and vision The importance of thoroughly evaluating the entire team, not just the founder Strategies for navigating cultural challenges and ensuring smooth transitions during acquisitions Why you should always do your own due diligence, even when trusting a source How to realistically evaluate market opportunities and competitive landscapes Mahati’s approach to investing in friends and family—no shortcuts allowed Timestamps: 00:00:00 – Mahati Sridhar on building relationships with founders 00:00:45 – Introduction: Investing in companies beyond the stock market 00:01:30 – Common mistakes investors make 00:02:15 – Angel investors vs. VCs: Different rubrics, same core principles 00:03:00 – Why investment is ultimately in the people, not just the idea 00:03:45 – How to gain conviction in founders: The power of relationships 00:05:00 – Learning from mistakes: The value of conversations outside of business 00:07:00 – The importance of assessing the entire team and not just the founder 00:08:00 – Uncovering cultural challenges by talking to team members 00:09:00 – Buying an entire company: The due diligence difference 00:10:00 – Strategies for smooth change management in acquisitions 00:13:00 – The critical role of over-communication during transitions 00:14:00 – The value of talking to customers during due diligence 00:15:00 – Evaluating personal investments: Trusting your source vs. due diligence 00:17:00 – Assessing market potential: Beyond the "billion-dollar" pitch 00:20:00 – Investing in friends and family: A critical lens 00:23:00 – Disaster story: The consequences of incomplete due diligence 00:26:00 – Final advice for investors: Understanding long hold times 00:27:00 – About Revolution's Rise of the Rest Seed Fund Connect with Mahati Sridhar and Revolution's Rise of the Rest: Website: revolution.com LinkedIn: Mahati Sridhar Deal Closers is brought to you by WebsiteClosers.com and produced by Walk West. Hosted on Acast. See acast.com/privacy for more information.

July 8, 202531 min

Smarter Checkout Strategies and Hidden Tech Debt, with Sarah Gallagher

Many Ecommerce brands believe their customer journey is optimized, but are they leaving significant revenue and trust on the table without even knowing it? From a clunky checkout to hidden technical debt, seemingly small issues can quietly erode profits and customer loyalty. In this episode of Deal Closers, we chat with Sarah Gallagher, CEO and Head of Strategy at Gamma Waves. Sarah has helped major brands like Nike and Airbnb, as well as fast-growing startups, build smarter Ecommerce foundations. She dives into how to create strategic checkout experiences, identify and eliminate hidden tech debt, and build scalable Ecommerce systems that drive growth. You’ll learn: Why a "good enough" checkout experience is actually a major revenue leak How to leverage the checkout process to build trust with new customers Practical strategies for "smarter upsells" that feel valuable, not "icky" What "technical debt" is and how it can silently sabotage your site's performance A real-world case study of a 37% conversion rate increase by simply cleaning up backend code Why AB testing is critically underutilized in Ecommerce and where to start The growing importance of "circular commerce" and how brands are owning the resale market How to get your hands around your data to unlock powerful insights Timestamps: 00:00:00 – The critical importance of understanding your data 00:00:30 – Introduction to Sarah Gallagher: The unsung hero of the customer journey 00:01:30 – Sarah's journey into digital commerce: From early 2000s to Gamma Waves 00:02:00 – Building the first Shaq Ecommerce site and Sony Latin America 00:04:00 – The evolving nature of Ecommerce and why customer experience always wins 00:05:00 – Why your checkout experience is a major revenue opportunity 00:06:00 – Building trust signals at checkout for new customers 00:07:00 – Case studies: Optimizing checkout for Flight Club and Supergoop 00:08:00 – Using AB testing to uncover hidden opportunities (and biases) 00:11:00 – The surprising results of an AB test: Percent vs. Dollar savings 00:12:00 – Implementing "smarter upsells" that genuinely add value 00:15:00 – Understanding and eliminating technical debt in your Ecommerce site 00:17:00 – The 37% conversion rate increase from a simple backend cleanup 00:19:00 – Why site audits are often neglected and their hidden value 00:20:00 – Long-term strategic planning and the concept of "circular commerce" 00:24:00 – The biggest "money leaks" in Ecommerce: Tech debt and lack of AB testing 00:25:00 – Where to start with AB testing for maximum impact 00:27:00 – What's next for Ecommerce brands: Getting a handle on their data 00:29:00 – How AI can help pull insights from clean data 00:30:00 – Connecting with Sarah Gallagher and Gamma Waves Connect with Sarah Gallagher: Website: gammawaves.io LinkedIn: Sarah Gallagher Deal Closers is brought to you by WebsiteClosers.com and produced by Walk West. Hosted on Acast. See acast.com/privacy for more information.

June 24, 202530 min

Mastering Key AI Tools in Ecommerce, with Ashley Gross

The world of AI is moving fast, and for Ecommerce founders, it’s easy to get lost in the hype or paralyzed by the possibilities. How do you cut through the noise and leverage AI to drive actual results for your business? In this episode of Deal Closers, we sit down with Ashley Gross, a leading AI consultant who has been helping companies implement practical AI solutions long before it was a mainstream topic. Ashley shares her playbook for Ecommerce founders and executives looking to move beyond "shiny object syndrome" and truly integrate AI into their strategy - from optimizing ad spend to revolutionizing search. You’ll learn: How to shift your mindset about AI from fear to strategic advantage The top three "money leaks" in e-commerce that AI can solve Why auditing your existing tech stack is crucial before implementing new AI tools How AI can automate repetitive tasks, freeing up your team for strategic work Practical ways to optimize ad spend and understand the full customer journey with AI The difference between "search engine optimization" and "answer engine optimization" and why it matters now more than ever Timestamps: 00:00:00 – The mindset shift: "Why didn't we do this sooner?" 00:01:00 – Introducing Ashley Gross: Making AI practical, not paralyzing 00:02:00 – Ashley's journey into AI: From marketer to AI innovator 00:04:00 – Overcoming AI fear: It’s emotional, not just technical 00:05:00 – Where e-commerce founders should start with AI 00:06:00 – Identifying and solving the "money leaks" in your business 00:08:00 – AI tools for data cleaning and enrichment 00:10:00 – Using AI for smooth tech stack migrations 00:12:00 – Automating repeatable tasks and simplifying customer data 00:13:00 – The realistic potential of reducing work hours with AI 00:14:00 – How AI can optimize your ad spend for better profitability 00:16:00 – Moving beyond vanity metrics to real customer insights with AI 00:18:00 – Connecting with Ashley Gross and her AI courses 00:19:00 – SEO vs. AEO: Optimizing for answer engines 00:21:00 – The importance of valuable, concise content for AI 00:24:00 – Avoiding "shiny object syndrome" in AI adoption 00:26:00 – The permission to "breathe" and optimize existing tools 00:27:00 – Final action item: Embrace the student mindset for AI success Connect with Ashley Gross: Website: theashleygross.com LinkedIn: Ashley Gross Deal Closers is brought to you by WebsiteClosers.com and produced by Walk West. Hosted on Acast. See acast.com/privacy for more information.

June 4, 20251 hr 1 min

23 Profitable Years in a Row + A Successful Exit: Daniel Bower's Web Agency Journey

What does it look like to build a business over two decades—with no outside investment, no years in the red, and no shortcuts? That's what Daniel Bower did, and today he shares his 23-year journey of growing a web development side hustle into a thriving digital marketing agency—and ultimately, selling it on his own terms. You’ll learn: Why steady growth and consistency can be more valuable than fast scale How to know when it’s the right time to leave your job and go all in The power of building a team that sticks with you for decades How to prepare your company for sale—while still running the business What buyers really care about in a founder-led business How WebsiteClosers.com helped Daniel find the perfect buyer match Timestamps: 00:01:42 – Launching a web development company in 2001 00:05:41 – When to take the leap from side hustle to full-time 00:13:30 – How a government connection led to a major client 00:18:22 – Evolving from website builder to full-service digital marketing 00:24:45 – How AI is changing the game—and who will survive 00:36:48 – Why Daniel decided it was time to sell 00:45:16 – How to prep your business for a smooth exit 00:54:26 – Training the buyer’s new team and embracing the transition 01:00:02 – Celebrating the sale with ski trips and next-chapter planning This episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West . Hosted on Acast. See acast.com/privacy for more information.

May 21, 202520 min

How to Sell a Marketing Agency, with Adam O'Leary

Selling a business is a monumental decision. There's excitement, self-reflection, and yes, uncertainty. For Adam O’Leary, founder of encite branding + marketing + creative , the journey to a successful exit was sparked by a realization - it was time for change. After nearly two decades of growing his full-service marketing agency from a one-man operation to a thriving business, Adam partnered with Website Closers to navigate the selling process. Despite initial doubts about his company’s value, Adam discovered a wealth of interest—over 100 inquiries poured in, and multiple serious discussions followed. The end result? A sale that exceeded expectations and opened new doors for his future. In this episode, Adam reflects on his journey, from the entrepreneurial leap that started it all to the challenges that inspired his decision to sell. He shares how Website Closers supported him every step of the way, offering candid advice, patient guidance, and an expertly managed process. For Adam, the experience validated years of hard work and provided a meaningful exit. Tune in to hear Adam’s candid story about: The “three B’s of exit” and why he decided it was time to sell. How he navigated the broker selection process and why Website Closers stood out. The surprising level of interest his company received and what it felt like to secure his first big business wire. Advice for entrepreneurs considering their own exit strategy. This episode of Deal Closers is hosted by Nate Lind, brought to you by WebsiteClosers.com, and is produced by Earfluence . Hosted on Acast. See acast.com/privacy for more information.

May 7, 202528 min

Why This D2C Founder Walked Away from His Thriving Business

Building a business is an incredible journey, but what happens when your passion for that business starts to fade? For Ellis Achim, founder of Paddie Nails , success in the D2C e-commerce space wasn’t enough—he wanted to build something he truly loved working on every day. After years of growing Paddie Nails into a thriving, profitable brand, Ellis realized that while the business was doing well, he wasn’t personally connected to the niche. So he decided to sell, but it wasn't a simple process. After a disappointing experience with another firm, he found Website Closers and worked with broker Paul Volen, who streamlined the process and connected him with over 100 serious buyers, ultimately leading to a successful sale. In this episode, Ellis shares: Why passion matters in long-term business success—and when to move on. The challenges of finding the right business broker (and what to avoid). How Website Closers' buyer network generated 106 NDA signings and 7 serious buyer calls. What it feels like to receive your first big business exit wire. This episode of Deal Closers is hosted by Nate Lind, brought to you by WebsiteClosers.com, and is produced by Earfluence . Hosted on Acast. See acast.com/privacy for more information.

April 29, 202533 min

Tariffs and Shipping in eCommerce, with Deliveri's Jason Brown

Between shifting trade policies, escalating tariffs, and unpredictable port delays, the political landscape is creating chaos for e-commerce businesses shipping internationally. What you could ship profitably yesterday might leave you stuck with massive unexpected fees today. In this episode of Deal Closers , we welcome Jason Brown, founder and CEO of Deliveri, a soon-to-launch platform aiming to give small and mid-sized e-commerce brands an edge. Jason shares how Deliveri helps founders navigate the volatile shipping environment — from skyrocketing costs to confusing customs processes — and why having a smarter logistics strategy isn’t just about saving money, it's about surviving. You’ll learn: How the ever-changing tariff environment is reshaping global e-commerce What "demurrage costs" are and how they can quietly destroy your margins Why most e-commerce founders are dangerously underestimating shipping’s impact on conversions How Deliveri is leveling the playing field with enterprise-level shipping rates for small brands What DDP vs DAP means — and why it could make or break your international sales Timestamps: 00:02:45 – How rising tariffs and political uncertainty are disrupting e-commerce 00:05:00 – What “demurrage costs” are — and why founders should be worried 00:13:02 – Could Mexico become the next major shipping hub? 00:16:03 – How Deliveri offers big shipping discounts to small businesses 00:20:13 – Jason Brown’s unexpected path from photonics engineer to e-commerce innovator 00:24:34 – Why logistics is the hidden killer of e-commerce conversions 00:30:54 – DDP vs DAP: The key to winning (or losing) international sales Resources & Links: Learn more about Deliveri: ondeliveri.com Explore how to sell your e-commerce business: WebsiteClosers.com This episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West . Hosted on Acast. See acast.com/privacy for more information.