Do Hard Things Podcast

Gabe Lullo
  • 5.0 (151)
  • Business

Meet Gabe Lullo. Gabe Lullo is the CEO of Alleyoop, a sales development agency working with industry giants such as ZoomInfo, Salesloft, and Adobe. He has trained over 8,000 salespeople across diverse businesses and, during his tenure in Alleyoop, he has personally hired and managed more than 1,500 SDRs. With over two decades of experience in sales, marketing, and executive recruitment, his strategies have significantly driven Alleyoop’s growth.

  1. 3d ago

    Do Hard Things A Podcast With Gabe Lullo Ft. Vel Johnson

    "When you know to do better, you do better." - Vel Johnson Vel grew up an Army brat, moving every two to three years, unpacking just long enough to start making friends before her father's next assignment came through.  Her late father earned a Bronze Star across two tours in Vietnam, and the discipline he ran the household with became the discipline she'd later run a business with.  What could have been destabilizing instead taught her to build community fast, wherever she landed, a skill that turned out to be the whole job once she got into PR. She left a stable career in Florida's legislative arena, sold her house, and started Vasaj Communications in a city where she knew no one, at the start of the Great Recession.  No plan B. Within two years, Black Enterprise magazine profiled her as "The Small Business Catalyst," unpaid, unsolicited, just a phone call she almost mistook for a prank. Two decades later, she led statewide bicentennial celebrations with over 200 events and got authors flown overseas off a single press release.  But the hardest thing she's done wasn't a campaign.  In 2024, while running the Tallahassee-Leon County Bicentennial for 300,000 residents, her mother passed away.  She buried her, drove five hours back, and was at work the next Monday.  Months later, she had hip replacement surgery and kept working through recovery, because the mission wasn't done. "I had to put the grief on hold. But we all have to decide whether we're going to keep showing up. That's what I decided to do."

    Do Hard Things A Podcast With Gabe Lullo Ft. Vel Johnson

  2. 5d ago

    Do Hard Things A Podcast With Gabe Lullo Ft. Michael Hanson

    "AI will make good salespeople better and bad salespeople worse. It just accelerates every trend." - Michael Hanson, CEO and Founder of Cosmic Growth Michael studied politics, not sales, cutting his teeth on an election campaign in South Africa before drifting into an account manager role at a London tech company.  He never chased sales for the money.  What pulled him in was the communication itself, and the version of himself it forced him to become: a better listener. He later ran growth for an outsourced BDR company with 300 reps in Colombia, watching sales teams book meetings his clients still couldn't close.  That gap is why he started training salespeople in 2019. His research keeps landing on the same number: only 18% of buyers trust salespeople, and most of what looks like a skills gap is really a lack of curiosity about the other person, whether that shows up as a copy-paste demo, a generic cold email, or a script read the same way to everyone. His framework opens with a lesson from Superman comics: sales dropped in the '70s once he became too invincible to relate to, and picked back up once writers gave him kryptonite.  Michael tells sales teams the same applies to them.  Being upfront about what you're not good at builds trust; pretending you're the best at everything doesn't. "Most sellers don't have a skills problem. They have a spiritual problem." He uses AI for research and editing, never for writing the whole pitch, because a fully AI-written post always ends up sounding like everyone else's.

    Do Hard Things A Podcast With Gabe Lullo Ft. Michael Hanson

  3. Aug 19

    Do Hard Things A Podcast With Gabe Lullo Ft. Marc Anthony Longwith

    "Everybody wants to be the hero. Nobody wants to walk the hero's journey." - Marc Anthony Longwith, Founder of Evolved Entrepreneur Marc grew up surrounded by addiction, the only person in his immediate family to graduate high school.  What pulled him out was martial arts, starting at 12, taking two buses and walking a mile to the gym on his own, becoming a black belt and coaching other fighters by 14.  That discipline became the identity everything else was built on. He worked his way from busboy to sommelier through some of the toughest kitchens in Las Vegas, then co-founded a brewpub that became one of downtown Vegas's top spots, backed in part by Tony Hsieh.  Then 2020 hit.  In a compressed window, he lost both parents, a relationship he thought would end in marriage, and the business, nearly all at once.  He calls what followed "the sacred collapse," not a motivational turnaround, just survival, day by day, for the better part of a year. What came out the other side was two seven-figure brands built and exited, real sobriety, and a coaching philosophy built on subtraction instead of addition: most people aren't missing a framework, they're carrying old patterns that block the skills they already have. "Some of us are just built a little different. But resilience isn't something you're born fully loaded with, it's built in layers, little by little, or you crush people before they're ready."

    Do Hard Things A Podcast With Gabe Lullo Ft. Marc Anthony Longwith

  4. Aug 17

    Do Hard Things A Podcast With Gabe Lullo Ft. Ryan O'Hara

    "The worst thing you could do is go look at what your competitors are doing and try to replicate what they just said on your website. You're just going to look like everybody else.” - Ryan O'Hara Ryan started as a video production intern at Dyn, hoping to make ads before pivoting into cold prospecting instead, becoming the company's first BDR.  He helped scale the sales team from three reps to over a hundred before Oracle acquired the company for north of $600 million. He carried the same instinct through LeadIQ: business messaging didn't have to be boring.  While the sales tech space drowned in "hit your number" energy, Ryan sent music videos to prospects and made 90s-style jingle ads for target accounts like Zoom and Logitech, then watched those videos rack up thousands of organic views from inside the exact companies he was trying to reach. His first Pitchfire venture nearly ended when his sole investor passed away from cancer mid-round.  He rebuilt it into a new company, investment infrastructure for VC firms still running deal flow through Typeform and Google Docs instead of anything built for it.  His read on outreach in the AI era hasn't changed: reply rates have crashed, AI-written pitches all sound the same, and what still breaks through is a real detail two humans actually have in common, not a value prop. "Be yourself the whole time. If you're an SDR who makes music, put music into your prospecting. Life doesn't have to be one octave lower just because you're at work."

    Do Hard Things A Podcast With Gabe Lullo Ft. Ryan O'Hara

  5. Aug 12

    Do Hard Things A Podcast With Gabe Lullo Ft. Michael Assraf

    "There's software replacing software, and now there's software taking over services. I don't think we've seen anything like this since the Industrial Revolution." - Michael Assraf, Founder of Flamingo Michael started in the Israeli infantry, then moved to logistics, managing budgets in the hundreds of millions at 18 years old with nothing but Excel macros to automate it.  That early responsibility, thrown at him before he was remotely ready, became the foundation for everything after.  He co-founded a cybersecurity startup in 2016, took nearly five years to find product-market fit, raised $60 million, and walked away as CEO after nine years, right as he felt AI was about to change what software even meant. His new company, Flamingo, targets a market most VCs don't even understand. Managed service providers, a $105 billion, deeply fragmented industry where 75 percent of MSPs run under $3 million in revenue with fewer than five people.  He'd learned firsthand that MSPs pay twice for the same problem, once to software vendors and once to technicians.  Flamingo was built to zero out the tooling cost using open-source infrastructure instead. Before shipping a single feature, he launched a free community and vendor directory called Open MSP.  No pitch, no sales ask, just a better way for MSPs to see what open-source alternatives existed for the tools they were already overpaying for.  It crossed 2,000 MSPs on the waitlist before the product even existed. "People are always suspicious when you give them something for free. But that's exactly the customer profile I was looking for: the ones willing to adopt open source."

    Do Hard Things A Podcast With Gabe Lullo Ft. Michael Assraf

  6. Aug 10

    Do Hard Things A Podcast With Gabe Lullo Ft. Yaron Vorona

    "It's easy to father a child. It's hard to be a dad. It's easy to be a founder. It's hard to be a leader." - Yaron Vorona, Founder Coach and Former VC      Yaron has a physics degree and an MBA from London Business School, an unusual pairing that came from wanting to build technologies that lead to a better future.  He's since founded and backed companies in cybersecurity, AI, blockchain, and defense across three continents, made most of the classic first-time-founder mistakes, ran a company out of cash, and eventually crossed to the VC side before coming back to work directly with founders.      His diagnosis after years on both sides of the table… What looks like a strategy problem or a team problem is almost always a leadership problem underneath.  The hardest tension he sees founders wrestle with isn't delegation or speed, it's fear.  Founders usually already know the right decision the moment they're faced with one.  Fear is what sends them looking for evidence to justify what they're already scared into believing.      He calls himself a "dad venturer" on purpose.  A founder who can't manage their relationship with their family or their own body can't lead a company at full capacity either.  Nutrition, movement, sleep, and the people at home aren't separate from the job, they're the foundation of it.      "No founder has ever looked back on what they built and said, 'I wish I had spent less time with my family.'"

    Do Hard Things A Podcast With Gabe Lullo Ft. Yaron Vorona

  7. Aug 6

    Do Hard Things A Podcast With Gabe Lullo Ft. Stephen Klein

    "Innovation is never born. It's forced into creation kicking and screaming against its will." - Stephen Klein, Founder and CEO of Curiouser AI Stephen sat in a Harvard Business School classroom in 1994 feeling dumber than he'd ever felt in his life, unable to follow a single thing his professor said for a month and a half.  The breakthrough wasn't a lower IQ, it was realizing he'd never actually learned how to think, that thinking itself was a craft you get better at with practice.  That idea sat with him for thirty years: what if technology could make us think more deeply instead of thinking for us? When large language models arrived, he watched the industry build the opposite.  Every company raced toward automation that replaces human thought.  So he built Curiouser AI around reflective AI, technology trained to ask questions back instead of just handing over answers. He didn't fully act on his own convictions until his 50s, when he stopped making decisions based on what strangers thought of him.  That shift is what let him build a 70,000-follower LinkedIn audience by breaking every algorithm rule in the book, posting at night, posting on weekends, saying things the industry didn't want said out loud. "There's no such thing as failure if you don't quit. Read the biographies of anyone you admire. Every one of them failed. What they didn't do was stop."

    Do Hard Things A Podcast With Gabe Lullo Ft. Stephen Klein

  8. Aug 4

    Do Hard Things A Podcast With Gabe Lullo Ft. Vahid Fakhr

    "You should convince investors about the problem, not the product. Most founders are so excited about what they built that they forget to prove who's actually bleeding in that market." - Vahid Fakhr, Co-Founder and CEO of Evalyze Vee spent ten years on the other side of the table in venture capital, reviewing more than a thousand pitch decks before he ever built anything himself.  The mistake he watched founders make over and over wasn't a bad product.  It was leading with the dashboard instead of the wound.  Convince someone the problem is real and painful first. The product comes after. Then he switched sides.  Being a founder, he says, is a genuinely lonely job in a way being a VC never prepared him for.  As an investor, he could reject a hundred people a week with a generic line and move on.  As a founder, every rejection landed personally. His advice on rejection: don't just close the laptop and walk away.  Ask for feedback. Ask to stay on an investor's radar with a monthly update.  Most founders treat a "no" as a dead end.  He treats it as the start of a relationship that might pay off eighteen months later, once the traction catches up to the pitch. "Most of the time, rejection isn't about you. It's about that specific fund, their timing, their portfolio. Take the no, and build the relationship anyway."

    Do Hard Things A Podcast With Gabe Lullo Ft. Vahid Fakhr
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5
out of 5
151 Ratings

About

Meet Gabe Lullo. Gabe Lullo is the CEO of Alleyoop, a sales development agency working with industry giants such as ZoomInfo, Salesloft, and Adobe. He has trained over 8,000 salespeople across diverse businesses and, during his tenure in Alleyoop, he has personally hired and managed more than 1,500 SDRs. With over two decades of experience in sales, marketing, and executive recruitment, his strategies have significantly driven Alleyoop’s growth.

Information

  • Creator
    Gabe Lullo
  • Years Active
    2024 - 2026
  • Episodes
    106
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 | All Rights Reserved | Gabe Lullo
  • Show Website
    Do Hard Things Podcast