Bridge the Gap™ by Revenue Reimagined

Adam Jay & Dale Zwizinski
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Mar 18, 2026 • 35min

Episode #137 Why Most SaaS Startups Fail After Building the Product | Alex Boyd

Is building the product actually the easiest part of your business?In this episode of Bridge the Gap, we sit down with Alex Boyd, co-founder of Wildfront and multi-time SaaS founder, to break down what founders are getting wrong right now. Building is not the bottleneck. Distribution, integrations, support, and trust are.We also dig into how AI is reshaping team structure and why the companies that win in the next era will be the ones that can execute after the launch, not just ship the code.Key Highlights✓ Why building the tool was never the hardest part of SaaS ✓ The “60% effort” problem and how AI changes the work that matters ✓ Why B2B buyers don't buy features, they buy a "throat to choke" ✓ The massive ROI difference between Founder Brand and paid ads ✓ Why a fat, healthy pipeline solves 90% of your business problems ✓ Transitioning from agency burnout to a buy, build, and hold SaaS portfolioIf you are a SaaS founder relying on product features instead of a real GTM motion, or a revenue leader trying to build a leaner, post-AI organization, this episode is for you.Connect with Alex - alexboydSponsor Info: We are proudly supported by Sendoso - Where Thoughtful Gifting Drives Results! Learn more about Sendoso today at https://www.sendoso.com…   🎁 Lastly, we have a gift for you! We’re tired of seeing people getting critical GTM components wrong. Need help with your ICP, Buyer Persona, and Value Prop? Tired of the shitty “resources” people “give away” to gain followers? We’ve developed a tool that creates your basic GTM Foundations (ICP, BP, abd Value Prop) for you. Snag it here.
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13 snips
Mar 11, 2026 • 39min

Episode #136 Your GTM Foundations Are Probably Wrong | Vihaar Nandigala

Vihaar Nandigala, co-founder of Orange Slice and builder of data-first GTM tools, explains why bloated all-in-one stacks fail. He discusses using a raw database as CRM, why timing outperforms personalization, moving from static lists to live scraping, and how AI will reshape prospecting and outbound practices.
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Mar 4, 2026 • 34min

Episode #135 How to Convert B2B Buyers Without Convincing Them | Kate Dileo

Kate DiLeo, founder and CEO of Kate DiLeo Branding who helps B2B and SaaS teams sharpen messaging. She breaks down the Brand Trifecta: tagline, value prop, differentiators. Short talks cover aligning personal and corporate brands, when leaders should be the public face, and why messaging should convert rather than convince.
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Feb 11, 2026 • 32min

Episode #134 Great Demos Still Lose Deals. Here’s Why | Mor Assouline

Why do good demos still result in ghosting?In this episode of Bridge the Gap, we sit down with Mor Assouline, Founder of Demo to Close, to break down why a flawless product walkthrough can still lead to a ‘maybe’ instead of a ‘yes,' and how to fix it using the art of ‘Unselling.’Key Highlights✓ The "Movie Trailer" Framework and why demos don’t close deals alone✓ Stop Feature Dumping: Solving problems vs. showing settings✓ How to use "Unselling" to build massive trust fast✓ The 3 gaps leading to bad demos: Self-doubt, results, and process✓ "Micro-Closing": How to to pulse-check alignment during the demo✓ How to ask about competitors without being awkwardIf you are an AE tired of happy ears or a sales leader trying to fix a leaky funnel, this episode is a gut check on your process.Connect with Mor - moreassoulineSponsor Info: We are proudly supported by Sendoso - Where Thoughtful Gifting Drives Results! Learn more about Sendoso today at https://www.sendoso.com…   🎁 Lastly, we have a gift for you! We’re tired of seeing people getting critical GTM components wrong. Need help with your ICP, Buyer Persona, and Value Prop? Tired of the shitty “resources” people “give away” to gain followers? We’ve developed a tool that creates your basic GTM Foundations (ICP, BP, abd Value Prop) for you. Snag it here.
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Feb 9, 2026 • 36min

Episode #112 This YC Startup Uses AI to Expose $500B Hidden Risks in Construction - Luigi La Corte

How do you fix an industry drowning in lawsuits and blown budgets? Luigi La Corte, co-founder & CEO of Provision (a Y Combinator–backed startup), joins us to share how his team is using AI to uncover risks hidden in construction documents.From managing multi-billion dollar infrastructure projects to building one of the most promising construction tech startups, Luigi talks: • Why contractors lose billions to hidden risks (and how AI can stop it) • His leap from civil engineering to YC founder • The future of AI-powered contract review • Lessons from early customers, sales, and scaling beyond product-market fitIf you’ve ever wondered how AI, construction, and entrepreneurship collide, this conversation is for you.Connect with Luigi: https://www.linkedin.com/in/luigi-r-la-cortePS - huge shout out to Sendoso for sponsoring our show.We could not do this without you.See how Sendoso can help increase pipeline, ROI, and customer retention.ag8KTRl2oVMGaryscYlq🎁 Lastly, we have a gift for you! We’re tired of seeing people getting critical GTM components wrong. Need help with your ICP, Buyer Persona, and Value Prop? Tired of the shitty “resources” people “give away” to gain followers? We’ve developed a tool that creates your basic GTM Foundations (ICP, BP, abd Value Prop) for you. Snag it here.
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Feb 9, 2026 • 34min

Episode #133 How Taelor Is Changing the $140B Men’s Fashion Market

Is personalization just a "nice-to-have" or the entire game?In this episode of Bridge the Gap, we sit down with Anya Cheng, Founder & CEO of Taelor, to explore how she’s using AI to change the $140B men’s fashion market without owning a single piece of inventory.We cover the harsh reality of moving from big tech giants to the founder trenches, the zero-inventory model, and how to use customer data to fix the massive waste problem in the fashion industry.Key Highlights✓ Why Go-To-Market strategies from Meta don’t work for startups ✓ The Tesla Rule: Selling the goal vs. the product ✓ How to build a zero-inventory model with high margins ✓ Solving decision fatigue for the 42% of men who hate shopping ✓ Using rental data to reduce landfill waste and help brands forecast If you are a founder looking for a wedge in a crowded market or a GTM leader wanting to understand the future of AI personalization, this episode is for you.Connect with Anya - anyachengSponsor Info: We are proudly supported by Sendoso - Where Thoughtful Gifting Drives Results! Learn more about Sendoso today at https://www.sendoso.com…   🎁 Lastly, we have a gift for you! We’re tired of seeing people getting critical GTM components wrong. Need help with your ICP, Buyer Persona, and Value Prop? Tired of the shitty “resources” people “give away” to gain followers? We’ve developed a tool that creates your basic GTM Foundations (ICP, BP, abd Value Prop) for you. Snag it here.
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16 snips
Jan 28, 2026 • 36min

Episode #132 Why Strategy Fails Without Execution (And How RevOps Holds It Together) | Nicole Brownell

Nicole Brownell, Managing Director of Growth and Value Creation at Novo Advisors and former COO/CPO, unpacks why go-to-market plans stall. She explores fragmented systems, misaligned KPIs, and product–marketing gaps. Nicole explains RevOps as the systemic glue that ties strategy to execution and outlines practical first steps for turnarounds and accountable, outcomes-focused work.
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Jan 14, 2026 • 33min

Episode #131 Why Tool Fragmentation Is Killing Your Go-To-Market Execution | Sayanta Ghosh

Are you drowning in tools but still starving for outcomes?In this episode of Bridge the Gap, we sit down with Sayanta Ghosh, Co-founder and CEO of NREV, to break down why the "27-tool tech stack" is slowing your growth and how to transition to a truly autonomous revenue stack.We cover the critical difference between deterministic workflows and agentic AI, why your pretty dashboards are a distraction from execution, and how to build a web of communication between humans and AI that actually scales.Key Highlights: ✓ Why the "27-tool login" is the biggest bottleneck in modern RevOps ✓ The "Stutter Test": Why most leaders can’t explain how their tools work together ✓ AI Workflows vs. AI Agents: When to use which for maximum ROI ✓ Why AI won’t fix broken data ✓ How to leverage "breadcrumb" data to outmaneuver competitors ✓ The future of 2026: Moving from massive departments to hyper-connected small teamsIf you lead RevOps, Sales, or Go-To-Market and want to stop the manual churn and start building an autonomous engine, this episode is for you.Connect with Sayanta - sayantaghoshSponsor info: We are proudly supported by Sendoso - Where Thoughtful Gifting Drives Results! Learn more about Sendoso today at https://www.sendoso.com…   🎁 Lastly, we have a gift for you! We’re tired of seeing people getting critical GTM components wrong. Need help with your ICP, Buyer Persona, and Value Prop? Tired of the shitty “resources” people “give away” to gain followers? We’ve developed a tool that creates your basic GTM Foundations (ICP, BP, abd Value Prop) for you. Snag it here.
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Jan 7, 2026 • 35min

Episode #130 Build AI Readiness First, Then Scale What Works (Enterprise) with Justin Trombold

Are you treating generative AI like a shortcut instead of a strategy?In this episode of Bridge the Gap, we sit down with Justin Trombold, founder and president of Antesyn Advisors, to break down how enterprise leaders can move past hype and build AI work that fits how the business actually runs.We cover readiness, process clarity, governance, and how to choose win-now plays without betting the company on experiments that will never scale.Key Highlights:✓ Why most AI strategies fail when they sit outside operations✓ Start with the problem first then match the right tech✓ Readiness signals: people, proficiency, collaboration governance, change muscle✓ Win now win later roadmap that leaders can actually run✓ How to turn pilots into repeatable programs with metricsIf you lead strategy, ops, or go to market and want AI work that creates measurable value, this episode is for you.Connect with Justin – / justintromboldSponsor info: We are proudly supported by Sendoso - Where Thoughtful Gifting Drives Results! Learn more about Sendoso today at https://www.sendoso.com…   🎁 Lastly, we have a gift for you! We’re tired of seeing people getting critical GTM components wrong. Need help with your ICP, Buyer Persona, and Value Prop? Tired of the shitty “resources” people “give away” to gain followers? We’ve developed a tool that creates your basic GTM Foundations (ICP, BP, abd Value Prop) for you. Snag it here.
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Dec 31, 2025 • 26min

Episode #129 2025 GTM Mistakes & What Not To Take Into 2026 (Year-End Recap) with Dale Zwizinski

Explore the fallout of the AI hype in 2025 and why focusing on outcomes is crucial. Discover the dangers of spam outreach and the importance of niche marketing. Learn how pipeline panic can derail growth and why foundational strategies still prevail amidst uncertainty. The discussion touches on leveraging deep discovery and problem-led messaging to close deals. Finally, predictions for 2026 highlight the rise of customer success roles and the need for leaders fluent in LLMs.

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