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.

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.

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.

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.

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.

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.

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.

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.