Startup Hypeman: The GOAT to Market Show

We’re gearing up for Season 5 but in the meantime, here’s the best of GTM season 3! What if instead of rushing to social media, paid ads, or even a traditional outbound sales motion, you used live events as a customer acquisition strategy? You immediately provide value to your target customer, create a shared experience, and get valuable face time with them. Sales Assembly has bootstrapped to 7-fi...

We’re gearing up for Season 5 but in the meantime, here’s the best of GTM season 3! If you're a CPG or retail brand, you know by default the importance of brand. It's what people buy into as much as the product itself. There's a reason why you choose to pay more for a Nike shirt when you could reasonably buy the same shirt without the logo. Brand is a promise. It's a value system. It's a marker of...

We’re gearing up for Season 5 but in the meantime, here’s the best of GTM season 3! Everyone wants to have a community. Everyone says they have a community. But just having a Slack or WhatsApp group doesn't actually mean you have community. Community is more about the interactions than the medium. And investing in community means playing the long game. Which is why so many brands don't think it's...

We’re gearing up for Season 5 but in the meantime, here’s the best of GTM season 3! What does it take to turn an idea for a boutique 7-11 into a tech-driven consumer market, into a national brand that merged with one of the biggest names in grocery? Enjoy this special episode, a replay of my interview with Foxtrot CEO & Cofounder Mike LaVitola live from the Startup Grind Chicago 4th Annual Gre...

We’re gearing up for Season 5 but in the meantime, here’s the best of GTM season 3! I think we can all agree AI is seemingly everywhere. But what does that actually mean for a startup? Enjoy this special episode, a replay of my interview with Techstars Managing Director Tricia Martinez-Saab live from the Startup Grind Chicago AI Showcase in November 2023. Tricia leads the AI and deep-tech vertical...

We’re gearing up for Season 5 but in the meantime, here’s the best of GTM season 3! The 3-letter acronym every startup obsesses with is TAM. But what is your TAM comprised of, and specifically WHO makes up your TAM? When you go to market, you may think your target is one group, but then find it includes others you weren't previously considering. That was the case for Cardio Diagnostics, who built...

We’re gearing up for Season 5 but in the meantime, here’s the best of GTM season 3! In a down economy, runway is everything. But it should also be everything in a boom economy. Great companies figure out how to spend less, and make more. Jordan Tepper cofounded the cocktail brand Apologue in 2017, and in the 7 years since he's achieved over $1M annual revenue, while raising just $2.5M in that time...

Part 2 of my conversation with Devin rolls on! After a 2-week break we regroup and picked up as if we never stopped. We found ourselves talking about how we handle managing time, playing the comparison game, not getting too caught up in outcomes while still pursuing them, and much more. Find Devin online: LinkedIn: https://www.linkedin.com/in/devinreed/ Instagram: https://www.instagram.com/thereed...

This episode was supposed to be about content creation (because Devin is a master at it — 2x Head of Content at unicorn startups Gong and Clari, 95k+ Linkedin followers, best B2B podcast in the game). But what I've always liked about the way this show runs is we don't fight momentum. Since Devin and I are so close personally, it's easy to gain momentum in unexpected places. And shortly after we be...

Most startups chase the next automation hack. Gabe Lullo built his by betting on people instead. As CEO of Alleyoop and host of the  Do Hard Things  podcast, he’s helped over 1,600 founders scale by focusing on one thing that never goes out of style—real human connection. From 11 million cold calls a year to rebuilding how companies hire, train, and lead SDRs, Gabe’s rethinking what growth actuall...

S4 BONUS! Creativity & Betting On Yourself - Reed Between The Lines We've got a special bonus for you this week! It's a re-airing of my appearance as a guest on the Reed Between The Lines podcast with my friend Devin Reed. I've done a lot of interviews in my life, and this is hands down my favorite one ever. We peel back the curtain on the transformation from Rajiv Nathan to 'RajNATION' and ge...

What if your startup’s biggest advantage isn’t your code, your speed, or even your traction but your ability to protect what’s yours? In a world where AI can replicate your idea in days, defensibility isn’t a luxury it’s survival. And few people understand that better than Bao Tran. Before founding Transformation VC, an IP-first venture capital firm, Bao built the patent strategy for Invasalign an...

Most sales advice today is either outdated or outright cringe. Meanwhile AI has made its way into every corner of life and business, and sales is no exception. Leslie Venetz is a rare (and deadly) combination of being a sales maestro, and on trend with technology. She's been employee #1 at multiple startups, sold into the likes of Kraft and AT&T, grown a TikTok account (@salestipstok) to 42k+...

Did you know some of the most iconic products and ideas in American history came out of the Great Depression? Not in spite of it — but because of it. In a time of scarcity, creativity thrived: Superman was born. Church bingo took off. Farmers started raising bullfrogs. And a banjo-playing dropout turned Scotch tape into a multi-million dollar business. All of this matters today as we face a period...

Did you know experts at Yale determined with up to 80% accuracy who would win a pitch competition purely based on the sound of their voice? It's not all about what you say, it's about how you say it. Your pitch, tone, rhythm, and even your breathing. Even a small shift can compeletely change perception. In fact, your voice might be your most overlooked go-to-market asset. One of the leading minds...

Madhav Bhandari helped take StoryLane from $900K to $8M in just 3 years. His approach? Don’t follow the playbook. Break it. We started this episode planning to talk about using your product to sell your product. But partway through, pattern interrupt marketing interrupted the episode itself — and we pivoted the whole conversation. From coffee carts with branded latte art to a mobile demo truck par...

Tired of pitches that fall flat? Ready to become the ONLY choice instead of just another option? This week on the GTM Show we've got a bonus episode — a replay of my appearance on the Expert Connexions Podcast at the 2025 Startup Grind Conference in Silicon Valley. Their host Julie Holton-Smith sat down with me on-site, and in this 10-minute lightning interview I share how to be the ONLY in your i...

Alisha Elenz went from cashier to prep cook to Executive Chef by 23. She became a two-time James Beard nominee, won Rising Chef of the Year, and cooked her way to Top Chef Season 21. But climbing the ranks wasn’t the finish line—building her own thing was. Now she runs Whisk the Night Away , a private dining company where she’s rewriting the rules as a chefpreneur. In this week’s episode—recorded...

You've heard of Go To Market. But have you heard of Go To CUSTOMER? GTC is going beyond getting the product in customer's hands and being intentional about the program(s) you build around the product to ensure uptake, produce successful outcomes, lower churn, and create advocates. It's the 'hidden' stuff that hedges against friction being your rate limiting factor. Sid Khaitan is an experienced pr...

If you were a PGA golfer you'd seemingly have the perfect career, right? Get paid to play golf, while playing on the best courses possible. From 5 years old, Soo Ahn worked his whole life to make it onto the PGA Tour. His hard work paid off when he got his Tour Card. He had made it into the top 1% of his field. But once he had 'made it', playing golf didn't play out as he had dreamed. So he made a...

What's your superpower? Every Founder has one. At the same time, not every founder has the SAME one. Which means just because Sara Blakely or Bill Gates did things one way, doesn't mean you also have to do things that way. When you know your superpower you can better make strategic decisions, acknowledge what should stay on your plate versus what you should delegate, and perhaps most importantly,...

Planning a fundraise? Then you need to know HOW to get in front of investors. Enjoy this special episode, a replay of my interview with Supply Change Capital Managing Partner Shayna Harris live from a Startup Grind Chicago event. Shayna shares what catches her eye, how funds are structured, the flow of money in a VC system, and why all that matters for founders. Original interview date: June 11, 2...

Baseball, hot dogs, apple pie, and...venture capital? In 2023 the Chicago Cubs spun off a fund by the name of Marquee Ventures. Marquee invests at the intersection of sports, media, commerce, and their enabling infrastructure. Enjoy this special episode, a replay of my interview with Marquee's Cofounder & Managing Partner Erik Hammer live from the Startup Grind Chicago 2nd Annual Health &...

One of the biggest struggles of an early stage startup is creating content. Or, really I should say creating GOOD content. It's pretty easy to publish a whitepaper that no one cares about, make Linkedin posts that don't get traction, or start a podcast but quit after 5 episodes. Creating content isn't hard, creating content that actually drives leads is hard. Erin Balsa is a content strategy exper...

Have you ever worked really hard on a piece of content, only for it to get like 5 likes online? It could be a bad distribution strategy or bad timing, but more likely it's because the content doesn't resonate. What if instead of approaching your content like a tech or product company, you approached it like a media company? Tyler Lessard didn't just approach it like a media company, he in fact lau...