Jay Baer sold out a full year of sponsorships before the website existed. 44 pitch calls. 45 days. Zero product built. He called it the most successful revenue initiative of his career.

That's not a fluke. That's three decades of professional marketing applied to something most people would have called a hobby.

Jay is a 7x New York Times bestselling author, one of the most in-demand keynote speakers in the world, and the founder of The Tequila Report which is a niche media brand he and his business partner Maddy built into a mid-six-figure business with 51,000 email subscribers and 32 consulting clients.

In this conversation, Jay breaks down what actually happened: how he evaluated the niche before it was a business, how he structured the pre-sell that funded a magazine before it launched, why he refuses clients who need content in two weeks, and what he tells anyone who wants to add a second revenue stream without blowing up what's already working.

He also delivers one of the most honest answers to the question founders avoid: should you turn your passion into a business? His answer isn't inspirational. It's accurate.

If you're a revenue leader, consultant, or entrepreneur thinking about a niche content play or a second income stream, this is the episode worth prioritizing this week.

Find Jay at jaybaer.com and subscribe to The Tequila Report at tequilareport.com/subscribe.

This episode is brought to you by Virtual Causeway. Visit virtualcauseway.com and mention the show for a special rate.

Your demand gen strategy might already be obsolete, and your buyers are the proof.

Kalyn Rozanski spent her career doing what most executives only claim to: seeing what's coming before it arrives. She co-founded a B2B innovation consultancy that grew to serve Starbucks, Procter & Gamble, and GlaxoSmithKline. At its peak, she stepped away to start over, because AI was reshaping the entire landscape, and she wanted to be on the right side of the shift.

In this episode of the Revenue Problem Solvers Podcast, Kalyn breaks down how AI has fundamentally changed where B2B buyers do their research, and why most revenue teams are still optimizing for a funnel that's already shifted. She explains the difference between demand generation and demand positioning, why trend intelligence belongs in every revenue leader's toolkit, and what a practical Monday morning rebuild actually looks like.

You'll hear her framework for testing AI sales tools using AppSumo, why month-to-month contracts are becoming the smarter strategic default, and why the decentralization of business may create more opportunity for founders and small teams than any previous era.

Sponsored by Virtual Causeway. Everything Kalyn talked about, buyers researching through AI, demand positioning over demand gen, that's the exact problem Virtual Causeway solves for B2B teams. virtualcauseway.com and mention the show for a special rate.

Your revenue problem might not be where you think it is.

Kyle McDowell spent nearly three decades inside Fortune 10 organizations running operations for tens of thousands of employees, and what he kept seeing had nothing to do with pipeline or product.

It was culture. Specifically, the gap between the values leaders posted on walls and the behaviour they actually modelled when pressure hit.

In this episode of the Revenue Problem Solvers Podcast, Kyle breaks down the operational side of revenue, how bespoke sales deals create execution failures that bleed clients and margins, why most corporate culture initiatives fail before they start, and how he built the 10 We's, a behavioural leadership framework designed to replace vague values with observable, accountable standards.

This is not a motivational talk. It is a practical conversation about why culture is a revenue lever, what it takes to build one that holds under pressure, and what leaders get catastrophically wrong when trying to change their teams.

Kyle is also the Wall Street Journal and USA Today bestselling author of Begin With We: 10 Principles for Building and Sustaining a Culture of Excellence, and his work spans industries from healthcare to financial services to tech.

If you lead a team and you have ever wondered why your culture initiatives never stick; this one is for you.

This episode is sponsored by Virtual Causeway. Shift from chasing cold leads to demand positioning that puts your brand in front of high-intent buyers. Visit virtualcauseway.com and mention Revenue Problem Solvers for a special rate.

Bob Jurkowski built the partner ecosystem at Intacct, scaled to hundreds of firms across multiple verticals, before the company was acquired by Sage for approximately $850M. He has helped build 11 B2B companies and consulted on partner strategy for companies as large as SAP. He now advises founders and executives on building predictable, capital-efficient revenue systems. Learn more at revenuegrowthstrategy.com.

In this episode of the Revenue Problem Solvers Podcast, Bob breaks down why partner programs universally underperform and lays out the architecture for building one that actually generates revenue.

Key takeaways: most programs are opportunistic by design and built to produce occasional deals at best. The embedded model is where real leverage lives. The partner scorecard is how you stop signing the wrong partners. Priming the pump with joint demand generation is what separates programs that launch from ones that die on paper. And crawl, walk, run is the right sequencing for any new partner relationship.

If your channel isn't producing or you're building your first program, this one is worth your full attention.

This episode is sponsored by Virtual Causeway. Visit virtualcauseway.com and mention the show for a special rate.

Your enablement team is a dumping ground.

Every department pushes change into the sales org and calls it enablement. No sequencing. No cascading. No intake. The "just send it to them, they'll figure it out" mentality does NOT work!Because they won't.

Andrew Quinn spent over a decade at HubSpot executing the playbook behind The Sales Acceleration Formula; except he was the one who actually had to make it work. He scaled HubSpot's sales enablement organization to a global team of 40 people and ran over 500 discrete enablement initiatives in a single year. All of them landed.

In this episode of the Revenue Problem Solvers Podcast, Andrew breaks down why enablement is a business discipline, not a department, how to build an intake process that protects your sales team from change fatigue, and the three things every enablement leader should do before building another piece of content.

If you lead a sales team, run enablement, or are building your GTM function for the first time, this one will change how you operate.

Sponsored by Virtual Causeway.

Stop chasing form fills and start showing up where buyers already are. Visit virtualcauseway.com and mention the show for a special rate.

Most sales professionals know LinkedIn matters. Very few know how to make it work.

Natasha Walstra spent a decade figuring out the difference, starting as an SDR who could not stomach cold calling car dealerships, discovering that connecting on LinkedIn before calling changed everything, and eventually training sales teams and building a framework she now calls the REALationship Growth Method.

In this conversation, she breaks down what separates people who get pipeline from LinkedIn from the ones who get ignored.

You will hear why your LinkedIn profile is likely costing you deals before you ever reach out, how to think about content as trust infrastructure rather than an audience play, and the exact sequence she uses to warm a cold contact into a ready conversation over time.

There is also a stat that should change how you think about LinkedIn opportunity: 1.2 billion users, less than 1% posting original content. If you are willing to show up like a human, the space is less competitive than you think.

This episode is sponsored by Virtual Causeway. If your demand gen isn't converting, they help revenue teams get found by buyers who are already looking. Visit virtualcauseway.com and mention the show for a special rate.

If you have 20 priorities, you actually have none.

That's the first thing Nate Littlewood tells founders when they come to him overwhelmed, overworked, and wondering why their revenue growth isn't showing up in the bank account.

Nate is a fractional CFO who took an unusual path to get here. He started on Wall Street as a top-ranked equity analyst, trained to tell the story the numbers actually say. Then he went and built something himself, co-founding Urban Leaf and bootstrapping a sustainable e-commerce brand from Kickstarter to seven figures.

Now he helps e-commerce and consumer packaged goods founders get profitable, get clear on their numbers, and identify the 2 or 3 things that will actually move the needle, instead of spinning on a list of 30.

In this conversation, Nate breaks down how he built his fractional CFO practice by niching down across three layers: role, stage, and vertical. He shares why most founders launching a consulting business waste time on websites and logos before they have a single client. And he names the financial blind spot that quietly kills founder-led businesses even when revenue is growing.

This is a practical, honest conversation about building a services business, getting profitable as a product company, and using financial clarity as a real competitive advantage.

This episode is sponsored by Virtual Causeway. They help revenue teams shift from chasing leads to showing up where buyers are already searching. Check them out at virtualcauseway.com and mention the show for a special rate.

Want more from Nate? Find him at futurereadycfo.com or connect with him on LinkedIn. He also hosts his own show, Profits On Purpose, where he breaks down the financial side of building a profitable business. Worth adding to your queue.

Most AI revenue projects fail before they start. The technology is not the problem. The data underneath it is.

Justin Shriber is the co-founder and CEO of Territ and a former VP at LinkedIn who has spent 25 years inside some of the most complex revenue organizations in tech, including Oracle and McKinsey. In this episode he breaks down the exact three-stage framework CROs should follow to deploy AI, measure real ROI, and grow revenue without simply adding headcount.

He walks through the real math: what it actually costs to hit 25% growth the old way versus the AI-driven way. The numbers will change how you think about your next hiring plan.

What you will take away from this conversation: why dirty CRM data kills AI projects before they launch, the three leading indicators that tell you AI is working before revenue moves, why the average rep only touches 60% of their accounts and what to do about it, and how to build a business case for AI investment that holds up in a boardroom.

This one is for CROs, founders, RevOps leaders, and anyone responsible for making AI pay off in a B2B sales org.

Revenue Problem Solvers Podcast is sponsored by Virtual Causeway.

#RevenueProblemSolversPodcast

Ross Paquette built Maropost into a global commerce and marketing platform over 13 years. No venture capital. No VP of Sales for longer than most founders would be comfortable admitting.

In this episode, Ross breaks down exactly how he built a revenue engine from scratch when he had no choice but to own it himself. He talks about the $30M ceiling he hit as a founder, the $8M in failed expansion attempts across Toronto and Chicago, and why most bootstrap founders make the same hiring mistakes over and over.

This is not a highlight reel. It is a real conversation about what it actually takes to go from startup to scale when you are running lean and every wrong hire sets you back months.

What you will hear in this episode:

Why founder-led sales drove explosive growth from $300K to $26M in under 30 months. The real cost of hiring before your system is ready. How Ross finally figured out his own ceiling as a founder and what he did about it. The shift from startup dictator to scale-up CEO and why that transition is harder than it sounds. Why he stopped selling candidates on the company and started filtering for the ones who could actually handle the reality. Three things every founder should do before posting that VP-level job.

If you are building a bootstrap business and trying to figure out how to grow revenue without unlimited runway, this episode was made for you.

Ross Paquette is the founder and CEO of Maropost. Find him on LinkedIn - https://www.linkedin.com/in/rossandrew1/ - or at maropost.com.

The Revenue Problem Solvers Podcast is hosted by Karl Ortmanns. New episodes drop weekly for founders, revenue leaders, and operators who are serious about building.

Sponsored by Virtual Causeway. Learn more at virtualcauseway.com.

#RevenueProblemSolversPodcast

Entrepreneurship, Sales, Business, SaaS, Marketing, Startups, Leadership, Management

AI isn’t just changing tools. It’s changing leadership.

In this episode of Revenue Problem Solvers, I sit down with fractional CRO and GTM advisor Neil Weitzman to unpack what change management really looks like in today’s AI-driven world.

After 25+ years building revenue engines at Rogers Media, Nielsen, and Deloitte, Neil has seen every kind of transformation. But AI may be the ultimate leadership test.

This conversation covers:

02:10 – Why change management feels harder than ever
05:30 – The two types of people inside every organization
09:45 – Why AI is different (and why it’s not)
13:40 – “Will” vs. “Skill”, the real career divider
18:25 – The power of direct, honest leadership conversations
23:10 – A story every leader needs to hear
28:50 – How individual contributors should show up
33:20 – Why some professionals won’t survive the AI shift
38:10 – The one action you should take this week
41:45 – Where to connect with Neil

If you’re a founder, CRO, sales leader, or revenue operator trying to navigate constant change, this episode will challenge how you think about growth, mindset, and leadership.

Because AI isn’t replacing leaders.

But it is exposing them.

Neil is a fractional CRO and GTM advisor who partners with founder-led B2B SaaS and technology companies to deliver speed, clarity, and zero drama. He is also a long-time Pavilion ambassador and works closely with consultants and fractional executives through the CAF community.

Connect with Neil:LinkedIn - https://www.linkedin.com/in/neilweitzman/
Linktree - https://linktr.ee/neilweitzman

This episode is sponsored by Virtual Causeway.

Traditional demand generation is breaking. Virtual Causeway helps revenue teams shift from demand generation to demand positioning, engineering where and how your brand appears when buyers research through AI tools and peer networks.

Learn more at virtualcauseway.com. Mention the show for a special rate.