Entrepreneurial legend and founder of CollegeHumor, Vimeo, and TeePublic, Josh Abramson, joins Adam Robinson on this episode of Unfuck My Startup. Josh shares his journey from building and selling CollegeHumor to IAC, to buying back Busted Tees and launching TeePublic. In this episode, you’ll hear Josh and Adam discuss the pros and cons of bootstrapping versus raising venture capital. Josh gets candid about the experience of selling a business and the importance of finding purpose in y...

Is "solving big, obvious problems" a recipe for failure? Peep Laja, founder of Wynter, joins us on Unf*ck My Startup to challenge classic business advice. We discuss why a small, profitable, bootstrapped company can be a bigger win for a founder than a VC-backed unicorn. In this deep dive, we explore: The VC Trap: Why a billion-dollar exit is an illusion and how VC-backed companies with "big, obvious" problems rarely succeed unless they have a massive war chest. The "David" Playbook: How...

This week on Unf*ck My Startup, we're joined by the team from Understory (Alex Fine, Chris Chambers, and Ali Yildirim) to dig into what’s really working in B2B SaaS advertising. 👉 Inside this episode: -A behind-the-scenes look at how Understory runs ads for B2B companies -A live walkthrough of RB2B’s campaigns in Miro -Audience members jumping on stage to get real-time feedback on their ads & outreach -Practical strategies you can use to improve targeting, creative, and performance ...

On this episode of Unf*ck My Startup, founders Adam Robinson (RB2B) and Max Greenwald (Warmly) go head-to-head, debating the two most popular startup paths: bootstrapping vs. VC funding. They've both built multi-million dollar companies in the same market, but with completely different approaches. In this debate, you'll learn: The Numbers: RB2B's $5.8M ARR with a team of 3 vs. Warmly's $4.4M ARR with 55 employees. The Philosophy: Why Adam chose to bootstrap for freedom and profitability, w...

In this episode of Unf*ck My Startup, Adam Robinson and Pete Crowley welcome Kyle Coleman, Global VP of Marketing at ClickUp, to dive into why outbound isn’t dead—but your outdated playbook is. We cover: -Why most outbound fails in 2025 -How buyer behavior has shifted -Real talk on cold outreach (and how to actually get responses) -The “Pitch Slap” live segment where founders try to out-book last week’s record of 35 demos -How Adam’s team is running their entire business with AI for 7 days ...

In this episode of UnF*ck My Startup, we sit down with Pukar Hamal, the founder of SecurityPal, who has defied the conventional VC playbook. Pukar shares the story of his last startup, where a mind-numbing 200-question security questionnaire almost killed a game-changing deal. That frustration led him to create SecurityPal, a company that literally does the work for you by having a team of 250 experts and AI to complete these questionnaires. He raised a $20M seed round from one of the best fi...

This week on UnF*ck My Startup, we sat down with Irina Novoselsky, the CEO of Hootsuite, to discuss her unique approach to personal branding and social media. Irina shares her journey from a Ukrainian refugee to leading a 1,500-person company, and why authentic, first-person content is a non-negotiable for modern leaders. If you've ever felt held back by the fear of "messing up" on social media or struggled with a blank page, this episode is for you. In this episode, you’ll learn: The Pow...

This week on UnF*ck My Startup, Adam Robinson and Pete Crowley welcome Taylor Haren, the mastermind behind sending millions of emails a month for companies like Fixer and RB2B! If you're wondering how to scale your cold email outreach, navigate the ever-changing spam filters, and get real results, this episode is for you. Inside this episode: -Infrastructure for Scale: Learn how to send 5,000 emails a day (and plan for 15,000) using 250 email accounts across 125 domains, and what happens...

This week on Unf*ck My Startup: We brought in Anthony Fletch—a full-stack B2B marketer who’s scaled GTM motions from both inside and outside the building. No VC burn. No unicorn fantasies. Just practical, tactical sh*t you can actually do if you’ve got a good product and a small team. We talk about outbound that converts, content that doesn’t suck, and how to run GTM without playing 2015 SaaS Mad Libs. Here’s how it goes down: 00:00 – Fletch intro, bad wifi, and Chicago shade 04:3...

This week on Unfck My Startup: We brought on a guy who built an AI startup, scaled to the moon, and sold it for $80M in cash… all in **six fcking months**. No hype. No headcount. Just a killer product, crazy timing, and a founder who moved faster than everyone else in the market. Maor breaks down exactly how it happened—from idea to acquisition—and takes live questions from the audience along the way. Here’s how it goes down: 00:00 – Who the f*ck is Maor and what did he build? 04:20 – ...

This week on UnF*ck My Start Up, we brought in the best-dressed man on LinkedIn — Emir Atli, CRO of HockeyStack. Emir breaks down how the smartest SaaS teams are using content, brand, and personal voice to generate real pipeline — without acting like a spammy leadgen bro. We talk playbooks, demand levers, and what founders need to understand before they hit scale. If you think brand doesn’t close deals, this one’s going to change your religion. Timestamps: 01:10 – The LinkedIn flywheel: why ...

Eric Siu (CEO of Single Grain and co-host of Marketing School with Neil Patel) joins UnF*ck My Start Up to deliver a marketing reality check. We dig into what’s actually working in B2B SaaS — and torch the tactics that should’ve been buried with Flash player. SEO? Dead. ABM? Evolving. Founder brand? Mandatory. This episode is a playbook for marketers who are done wasting budget on channels that don’t convert. Timestamps: 00:45 – Why SEO isn’t what it used to be 07:30 – The marketing strateg...

Unf*ck My Startup: Jason Bay Returns Last year, this episode broke our inbox. Jason Bay was that good. So we brought him back. Jason’s the guy behind sales orgs at ZoomInfo and Gong. He’s trained over 1,000 reps. And he breaks down outbound like a damn scientist — no fluff, no bro-hacks, just frameworks that print pipeline. If you're tired of guessing what works in outbound, start here. What we get into: – The new 3-message cold outreach framework that’s winning in 2025 – How to ...

Welcome to Unf*ck My Startup Not another sales podcast. Not another playbook dump. This is raw, live, no-fluff SaaS therapy — for founders, by founders. This week: Scott Leese. 6x sales leader5x founder3x author12 unicorns$25M ARR whispererScott’s helped more startups scale than your favorite sales bro has LinkedIn posts. He’s here to break down what’s actually working — and what’s killing your momentum. What we get into: – Why early GTM fails (and how to stop lighting budget on fire) ...

This week on Unf*ck My Startup: We had a last-minute guest swap, but trust me—Taylor Haren delivered. He’s the cold email assassin behind one of the fastest-growing campaigns we’ve ever seen: Fixer went from $1M to $10M ARR in 6 months, almost entirely from outbound. We break down the exact emails, the setup, the send logic, and the secrets behind 4 million emails a month that actually work. Here’s how it goes down: 00:00 – Why Taylor’s back (and what’s changed since last time) 01:15 ...

🎙️ Special Episode: My $70M Exit Collapsed Days Before Signing Hey everyone, Adam Robinson here. I recently joined Sam Parr and Harry Morton on the Moneywise podcast to share the unfiltered story of how a $70 million exit deal for my company fell apart just days before signing. We delved into the financial missteps I made—like prematurely spending millions on land, crypto, and a new mortgage—and the unexpected 60% tax bill that followed. More importantly, we discussed how this near-disaster b...

This week on Unf*ck My Startup: We brought in the guy everyone pretends to be—Nathan Barry. No VC fairy dust. No growth hacks. Just a dude who built a $40M+ ARR company (ConvertKit → now Kit) by actually doing the work and giving a sh*t about creators. We get into why most founders are LARPing as CEOs… and how Nathan scaled a real business without selling his soul. Here's how it goes down: 00:00 – Who the fck is Nathan Barry (and why I care) 03:40 – From $0 to Kit: how ConvertKit became the...

🎙️ The Cold Email Doctor is IN: How to Outbound Like a Pro in 2025 ❄️💉 Everyone wants to know: What’s still working in cold email? And this week, we brought in the guy who’s got more data than anyone else in the game—Vaibhav Namburi, founder of Smartlead and a certified beast when it comes to cold outreach. He’s not just running a $20M+ ARR bootstrapped SaaS company—he’s rewriting the rules of outbound with actual results, not recycled LinkedIn takes. 🔥 In this episode, we dig into: Why your ...

🎙️ How I Bootstrapped to $14M Profit and Found Real Product Market Fit Most founders are chasing Series A headlines. I’m chasing $14M a year in actual profit. I joined The Product Market Fit Podcast to talk about how I went from stuck at $3M ARR with a dying product... to launching Retention.com, hitting escape velocity, and scaling RB2B to nearly $5M ARR in under a year—all with a 5-person team. 🚨 We cover everything I wish someone had told me years ago: Why “fake” product market fit is kill...

422 people showed up expecting chaos—and got a sales masterclass instead. This week on Unf*ck My Startup: Kevin Dorsey literally Ubers in from the airport and delivers gold A surprise founder gets called off the bench to pitch LIVE 20+ demos booked on the spot Adam and Pete try (and fail) not to roast Rick Rubin If you sell anything, manage sellers, or are building a company in public—this is your blueprint. It’s gritty, chaotic, and weirdly inspiring. 👇 Watch it. Steal from it. Share ...