The Deal Closers Podcast

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.

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-commerceWhat "demurrage costs" are and how they can quietly destroy your marginsWhy most e-commerce founders are dangerously underestimating shipping’s impact on conversionsHow Deliveri is leveling the playing field with enterprise-level shipping rates for small brandsWhat DDP vs DAP means — and why it could make or break your international salesTimestamps:00:02:45 – How rising tariffs and political uncertainty are disrupting e-commerce00:05:00 – What “demurrage costs” are — and why founders should be worried00:13:02 – Could Mexico become the next major shipping hub?00:16:03 – How Deliveri offers big shipping discounts to small businesses00:20:13 – Jason Brown’s unexpected path from photonics engineer to e-commerce innovator00:24:34 – Why logistics is the hidden killer of e-commerce conversions00:30:54 – DDP vs DAP: The key to winning (or losing) international salesResources & Links:Learn more about Deliveri: ondeliveri.comExplore how to sell your e-commerce business: WebsiteClosers.comThis episode of Deal Closers is hosted by Jason Gillikin, brought to you by WebsiteClosers.com, and is produced by Walk West.

Pitching to investors isn’t just about having the next billion-dollar idea. It’s about energy, authenticity, preparation—and knowing your numbers.Today's episode of Deal Closers comes to you from recorded live at CED’s Venture Connect, where host Jason Gillikin sits down with two seasoned investors:Zakiya Alta Lee-Hill, Principal at Idea Fund PartnersNikin Shah, General Partner at Front Porch VenturesTogether, they share exactly what makes founders stand out in a pitch meeting—and what makes investors quickly say no. If you’re gearing up to raise capital or sell your company, this is essential listening.You’ll learn:Why VC money is like rocket fuel—and how it can blow up your business if you’re not readyHow much energy is too much energy in a pitchWhy authenticity and self-awareness beat hype every timeWhat to say when you don’t know the answerHow to prep for questions about your numbers, your tech, and your teamThe importance of targeting the right investors—and how to make it easy for them to help youTimestamps:00:00:03 – What VC dollars really mean for your company00:01:15 – First impressions and the importance of energy00:04:00 – Why excitement looks different for every founder00:07:51 – Know enough about every part of your business00:11:00 – Investors expect you to know your numbers00:13:56 – Is your market size actually realistic?00:17:09 – What problem are you solving, and why you?00:22:31 – Walk in saying, “I’m the company you’re looking for”Connect with the Guests:Nikin Shah – Front Porch VenturesZakiya Alta Lee-Hill, Idea Fund PartnersDeal Closers is brought to you by WebsiteClosers.com and produced by Walk West.