The Deal Closers Podcast

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 modelHow to use a crowdfunding campaign to validate an idea, raise capital, and find your first 2,000 customersThe "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 makeHow to build a profitable, multimillion-dollar brand without high overhead, a massive team, or an officeWhy obsessive product quality is the ultimate marketing strategy for a direct-to-consumer brandTimestamps 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 marketingThis episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West.

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 priceThe difference between running a business and "purpose-building" it for a future exitWhy it’s crucial to have your financials and data room in order long before you decide to sellThe importance of working with a broker you trust to vet buyers and navigate a complex, emotional processHow one deal broke—and how having the right team in place saved the saleWhat buyers look for in a company, from its operational health to its team cultureTimestamps 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 EricThis episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West.

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 businessThe pros and cons of bootstrapping your brand to millions in revenueThe devastating impact of a domain hack and how to protect your businessWhy "off-peak" sales seasons can present the biggest challengesHow to find the right broker who will be a "therapist" through the emotional journey of sellingThe surprising benefits of a fast sale with a strategic buyerThe joy of staying on with the new company and focusing only on the work you loveTimestamps: 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 sonFor 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.

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. VCsWhy investing in early-stage companies is fundamentally about investing in peopleHow to build genuine relationships with founders to assess their resilience and visionThe importance of thoroughly evaluating the entire team, not just the founderStrategies for navigating cultural challenges and ensuring smooth transitions during acquisitionsWhy you should always do your own due diligence, even when trusting a sourceHow to realistically evaluate market opportunities and competitive landscapesMahati’s approach to investing in friends and family—no shortcuts allowedTimestamps:00:00:00 – Mahati Sridhar on building relationships with founders00:00:45 – Introduction: Investing in companies beyond the stock market00:01:30 – Common mistakes investors make00:02:15 – Angel investors vs. VCs: Different rubrics, same core principles00:03:00 – Why investment is ultimately in the people, not just the idea00:03:45 – How to gain conviction in founders: The power of relationships00:05:00 – Learning from mistakes: The value of conversations outside of business00:07:00 – The importance of assessing the entire team and not just the founder00:08:00 – Uncovering cultural challenges by talking to team members00:09:00 – Buying an entire company: The due diligence difference00:10:00 – Strategies for smooth change management in acquisitions00:13:00 – The critical role of over-communication during transitions00:14:00 – The value of talking to customers during due diligence00:15:00 – Evaluating personal investments: Trusting your source vs. due diligence00:17:00 – Assessing market potential: Beyond the "billion-dollar" pitch00:20:00 – Investing in friends and family: A critical lens00:23:00 – Disaster story: The consequences of incomplete due diligence00:26:00 – Final advice for investors: Understanding long hold times00:27:00 – About Revolution's Rise of the Rest Seed FundConnect with Mahati Sridhar and Revolution's Rise of the Rest:Website: revolution.comLinkedIn: Mahati SridharDeal Closers is brought to you by WebsiteClosers.com and produced by Walk West.

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 leakHow to leverage the checkout process to build trust with new customersPractical strategies for "smarter upsells" that feel valuable, not "icky"What "technical debt" is and how it can silently sabotage your site's performanceA real-world case study of a 37% conversion rate increase by simply cleaning up backend codeWhy AB testing is critically underutilized in Ecommerce and where to startThe growing importance of "circular commerce" and how brands are owning the resale marketHow to get your hands around your data to unlock powerful insightsTimestamps:00:00:00 – The critical importance of understanding your data00:00:30 – Introduction to Sarah Gallagher: The unsung hero of the customer journey00:01:30 – Sarah's journey into digital commerce: From early 2000s to Gamma Waves00:02:00 – Building the first Shaq Ecommerce site and Sony Latin America00:04:00 – The evolving nature of Ecommerce and why customer experience always wins00:05:00 – Why your checkout experience is a major revenue opportunity00:06:00 – Building trust signals at checkout for new customers00:07:00 – Case studies: Optimizing checkout for Flight Club and Supergoop00:08:00 – Using AB testing to uncover hidden opportunities (and biases)00:11:00 – The surprising results of an AB test: Percent vs. Dollar savings00:12:00 – Implementing "smarter upsells" that genuinely add value00:15:00 – Understanding and eliminating technical debt in your Ecommerce site00:17:00 – The 37% conversion rate increase from a simple backend cleanup00:19:00 – Why site audits are often neglected and their hidden value00:20:00 – 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 testing00:25:00 – Where to start with AB testing for maximum impact00:27:00 – What's next for Ecommerce brands: Getting a handle on their data00:29:00 – How AI can help pull insights from clean data00:30:00 – Connecting with Sarah Gallagher and Gamma WavesConnect with Sarah Gallagher:Website: gammawaves.ioLinkedIn: Sarah GallagherDeal Closers is brought to you by WebsiteClosers.com and produced by Walk West.

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 advantageThe top three "money leaks" in e-commerce that AI can solveWhy auditing your existing tech stack is crucial before implementing new AI toolsHow AI can automate repetitive tasks, freeing up your team for strategic workPractical ways to optimize ad spend and understand the full customer journey with AIThe difference between "search engine optimization" and "answer engine optimization" and why it matters now more than everTimestamps:00:00:00 – The mindset shift: "Why didn't we do this sooner?"00:01:00 – Introducing Ashley Gross: Making AI practical, not paralyzing00:02:00 – Ashley's journey into AI: From marketer to AI innovator00:04:00 – Overcoming AI fear: It’s emotional, not just technical00:05:00 – Where e-commerce founders should start with AI00:06:00 – Identifying and solving the "money leaks" in your business00:08:00 – AI tools for data cleaning and enrichment00:10:00 – Using AI for smooth tech stack migrations00:12:00 – Automating repeatable tasks and simplifying customer data00:13:00 – The realistic potential of reducing work hours with AI00:14:00 – How AI can optimize your ad spend for better profitability00:16:00 – Moving beyond vanity metrics to real customer insights with AI00:18:00 – Connecting with Ashley Gross and her AI courses00:19:00 – SEO vs. AEO: Optimizing for answer engines00:21:00 – The importance of valuable, concise content for AI00:24:00 – Avoiding "shiny object syndrome" in AI adoption00:26:00 – The permission to "breathe" and optimize existing tools00:27:00 – Final action item: Embrace the student mindset for AI successConnect with Ashley Gross:Website: theashleygross.comLinkedIn: Ashley GrossDeal Closers is brought to you by WebsiteClosers.com and produced by Walk West.

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 scaleHow to know when it’s the right time to leave your job and go all inThe power of building a team that sticks with you for decadesHow to prepare your company for sale—while still running the businessWhat buyers really care about in a founder-led businessHow WebsiteClosers.com helped Daniel find the perfect buyer matchTimestamps:00:01:42 – Launching a web development company in 200100:05:41 – When to take the leap from side hustle to full-time00:13:30 – How a government connection led to a major client00:18:22 – Evolving from website builder to full-service digital marketing00:24:45 – How AI is changing the game—and who will survive00:36:48 – Why Daniel decided it was time to sell00:45:16 – How to prep your business for a smooth exit00:54:26 – Training the buyer’s new team and embracing the transition01:00:02 – Celebrating the sale with ski trips and next-chapter planningThis episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West.

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.

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.