Do Hard Things Podcast

Gabe Lullo

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. 1d ago

    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

  2. 3d ago

    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

  3. 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

  4. 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

  5. Jul 29

    Do Hard Things A Podcast With Gabe Lullo Ft. Evin Schwartz

    "No one has ever asked me for my diploma or my GPA. Show me the journey, not the destination." - Evin Schwartz      Evin never worked corporate for more than two weeks.  He built his first agency straight out of college, then found himself drawn into K-12 education after watching schools hand kids the same outdated curriculum he'd grown up with, decades removed from the world those kids would actually enter.  His question was simple: what if instead of building a new curriculum, we just helped kids connect with each other as humans first?      That question became Beluga, a global social learning platform now used by learners in over 120 countries.  It started with cold DMs to 50 award-winning teachers. Five responded.  Those five became the platform's first users, and Beluga has never spent a dollar on external marketing since.      One of the earliest moments that proved the model: a classroom in Missouri video-called a classroom in South Korea at nine at night.  A kid in South Korea said he loved basketball.  The room in St. Louis erupted like they'd won a championship, because a kid an ocean away had just become instantly familiar.  That's the wall Evin has spent his career trying to bring down.      His argument for reimagining education isn't anti-testing, it's pro-human.

    Do Hard Things A Podcast With Gabe Lullo Ft. Evin Schwartz

  6. Jul 28

    Do Hard Things A Podcast With Gabe Lullo Ft. Ned and Jamie Arick

    "Jamie looked at me and said, 'Get the SDRs to call on Saturdays. You're an idiot.' We doubled our revenue because of that one sentence." - Ned and Jamie Arick  Ned and Jamie are married and both run revenue at a high level, in different companies, at the same time.  Jamie's first SaaS job came from a Craigslist ad that sent her to a sketchy beach house where the whole team worked out of the attic.  Ned left a comfortable consulting career to start an HVAC company in Greensboro, North Carolina, a business neither of them knew the first thing about.  Eighteen months later, it had scaled to eight figures and exited for real money last July. What got them there wasn't a clever trick.  It was refusing to overcomplicate things.  When deals stopped closing on Mondays and Tuesdays, the fix wasn't a new methodology, it was simply having reps call on Saturdays so the calendar was already full by the start of the week.  When something breaks, Ned's first move is never to blame the person, it's to look at the process. Jamie brings the same philosophy from competitive bodybuilding: if something is working, you don't touch it for the sake of touching it.  You stay the course instead of quitting the moment it gets hard. "You attract what you are. If people don't understand why you work as hard as you do, you don't cut them out, you just spend less time with them and more time around people on the same path."

    Do Hard Things A Podcast With Gabe Lullo Ft. Ned and Jamie Arick

  7. Jul 22

    Do Hard Things A Podcast With Gabe Lullo Ft. Joey GIlkey

    "If you believe in the phone, you know that when you get people on it, it works. We just have to get you talking to the right 20 percent instead of wasting effort on the rest." - Joey Gilkey, Founder and CEO of Titan X Joey launched Titan X in June 2024 with no venture capital.  He hit $5 million in ARR in year one, acquired FrontSpin, and closed a $27 million Series A, all after proving the model worked, not before. His thesis is a vote of confidence in the phone, not a eulogy for it.  While the industry chased parallel dialers and higher call volume and watched connect rates slide anyway, Joey bet on the opposite: the phone still works, and works well, once you know who's actually going to pick up. His guarantee backs that belief with real money: 300 percent higher connect rates in the pilot, or he pays the client $10,000, no questions asked.  Out of roughly 500 contracts with that guarantee attached, only two clients ever tried to collect, and both turned out to be measuring their results wrong.  The phone delivered every time. The case he makes is refreshingly hopeful once you follow the math: when connect rates quadruple on the same number of dials, cost per meeting and cost per deal drop dramatically, and the phone becomes one of the most efficient channels a sales team has.  That's the argument that turned skeptics like Kevin Dorsey, who once dismissed the whole idea as too good to be true, into the platform's loudest advocates. "Only about 20 percent of any market will answer an unknown number. Find that 20 percent, and the phone becomes the highest-leverage channel you've got."

    Do Hard Things A Podcast With Gabe Lullo Ft. Joey GIlkey

  8. Jul 20

    Do Hard Things A Podcast With Gabe Lullo Ft. Robin Dimond

    "When I say it cost everything, it also cost a lot of relationships. People said, 'This is the dumbest thing you can do,' and family and friends stepped away from me." - Robin Dimond, CEO and Founder of Fifth & Cor Robin built Fifth & Cor fully self-funded. No investors, no safety net.  She leveraged her home and her car to get it off the ground, because loans weren't accessible and private equity meant giving away decision-making before she'd even started.  When people asked how they'd know she'd show up, her answer was simple: she wouldn't have a house if this didn't work. The early years cost her more than money.  She's been the janitor and the CEO in the same hour.  She's had trusted employees steal from her, one of them someone she'd stood beside at their own wedding.  She still hasn't stopped apologizing for the missed family moments, and says she hopes she never does, because that's what keeps her honest about the cost. What kept her going wasn't willpower.  It was knowing how many other lives were tied to the decision: employees with mortgages, clients trusting her with their brand, partners counting on the relationship.  On the days she wanted to quit, that ripple effect was the reason she got up anyway. "I've started over from zero more than once. What's the other option? Sit in bed and cry? You build, and you build better, even when you're scared to lose it all again."

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5
out of 5
201 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
    102
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 | All Rights Reserved | Gabe Lullo
  • Show Website
    Do Hard Things Podcast

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