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. 2h ago

    Do Hard Things A Podcast With Gabe Lullo Ft. Alex Seiler

    "Don't make an assumption, ask the question. Ask your senior people two things: what's slowing you down, and what would make you consider leaving. That pattern is your real priority list." -  Alex Seiler Alex's HR career started with a job creating employee ID numbers by hand at Citigroup.  Nobody dreams of being the employee ID guy, but he paid attention to what he was good at and let that pull him forward.  He still respects the people who do the unglamorous work the whole company depends on. From there he worked across Citi, WeWork, and Control Risks, and he's blunt about what that taught him: every size of company has its own flavor of chaos.  Bring startup speed to a battleship and you blow past every stakeholder.  Bring the battleship process to a five-person startup and you bore everyone into quitting.  The skill that transfers is judgment about pace, and diagnosing the environment before you prescribe anything. His rule for earning a seat at the table: lead with the business question, not the HR program.  He doesn't pitch leadership development to a CEO as a way to lift engagement scores.  He opens with the two VPs the company lost last year and what it cost to backfill them.  As CPO, he brought recruiting in-house, saved $500K, and put $360K of it into better benefits. His hot take: companies buy engagement software to fix a management problem.  The survey says people are unhappy with their manager, and the action plan is to run the survey again next quarter.  The data was never missing. The willingness to have an uncomfortable conversation was. "CEOs don't fund feelings. They fund downside protection and upside acceleration."

    Do Hard Things A Podcast With Gabe Lullo Ft. Alex Seiler

  2. 2d ago

    Do Hard Things A Podcast With Gabe Lullo Ft. Cris D'Annunzio

    "I wasn't making myself an NFL player. I was making myself behave like an NFL player before anybody believed that I could do it." - Cris D'Annunzio Cris spent three years buried on Princeton's depth chart, bitter and barely playing, to the point of calling Joe Paterno to ask about transferring to Penn State.  He stayed only because he'd never quit anything in his life.  Once the hope of football working out left the room, his ego left with it, and he started writing everything down, tracking every input, with no expectation it would lead anywhere. It led to an honorable mention All-Ivy League season and a shot in the NFL.  Then Wall Street, managing over $500 million in client assets.  Then thirty years as a working actor (American Gangster, Seinfeld, Animal Kingdom) in an industry that rejects you more than nine times out of ten.  Then high-ticket sales, where he still closes every week. His conclusion after all four arena's: talent was never the gap.  The gap is whether you keep the process intact when nobody's watching and everything in you wants to negotiate it away.  It's the premise behind Metal and Method: you don't know what you actually do every day, you know what you think you do, and your mind lies to you most in moments of duress. "At some point you will actually break. You can't do it yourself. This is why validation is so important."

    Do Hard Things A Podcast With Gabe Lullo Ft. Cris D'Annunzio

  3. Sep 30

    Do Hard Things A Podcast With Gabe Lullo Ft. Dave Slagle

    "Be authentic and tell the truth. In the end, people buy from people they know, like, and trust. Trust is the one thing our industry doesn't have a lot of." -  Dave Slagle, Founder of ICON Dave grew up in Berkeley in the '70s, around parents who treated nutrition and supplements as normal, and spent his teenage years as a competitive powerlifter.  He landed his first supplement industry job almost by accident, hired at one of the earliest Whole Foods Markets in the early '90s because of his grocery background, not his health science degree. Thirty years later, he's worked every link of the supplement supply chain, retail counter, raw materials, contract manufacturing, clinical trials, and now runs a nonprofit built to defend one ingredient… creatine.  His reason is blunt.  The industry is full of marketing puffery around creatine gummies, bars, and drinks with no public data proving the creatine survives heat, moisture, or shelf life, layered on top of decades-old myths that creatine is a steroid or causes weight gain.  So he partnered with an independent testing lab to certify batch-level purity, because he wasn't willing to accept purity claims he considered mathematically impossible without proof. He calls himself an "ageless athlete," borrowing the term from a philosophy he says most people get backwards: health span and strength span matter more than lifespan, and America is good at keeping sick people alive but bad at keeping healthy people healthy. "If you want a recurring customer base and a good reputation in this industry, be authentic. Tell the truth. You may not close every deal, but you'll build one that lasts."

    Do Hard Things A Podcast With Gabe Lullo Ft. Dave Slagle

  4. Sep 28

    Do Hard Things A Podcast With Gabe Lullo Ft. Brian Martynowicz

    "Companies are built by people, a lot of people, who care. Name me the five key employees responsible for Amazon. You can't. That's actually kind of problematic." - Brian Martynowicz Brian spent nearly two decades in enterprise technology, working as the family IT guy turned pre-sales engineer, watching a familiar pattern. Technical people who thought little of everyone else, and everyone else who thought technology was out of reach. He didn't see a skills gap. He saw a communication problem, and he became the guy who could bridge it. He went full-time on his personal content AI company in January, but not entirely by choice. He'd just helped a cybersecurity company raise nearly $20 million, then got fired for "performance reasons." With a side project already in motion, he gave himself six months to make it real or go back to the workforce. That project became Latitude, built around what he calls GTM engineering, the discipline of keeping a product's story intact as it passes through more and more hands without turning into a game of telephone. His own results: engagement up 1,100% this year, not from better writing, but from consistency. He's blunt about the tradeoff for that consistency: transparency, posting his MRR and his failures to thousands of strangers, which he admits is uncomfortable but has been "undeniable" for the business. "People don't buy software for features. They buy it because it solves a problem for them, and they stay because of why it exists."

    Do Hard Things A Podcast With Gabe Lullo Ft. Brian Martynowicz

  5. Sep 23

    Do Hard Things A Podcast With Gabe Lullo Ft. Julian Treasure

    "Everybody's listening is unique. Almost nobody understands that. Everybody goes around thinking, well, everybody listens like I do. No, they don't." - Julian Treasure, Sound and Communication ExpertJulian's relationship with sound started at six years old, and through years of playing in bands he developed multi-track listening, paying close attention to everything around him at once. He spent years running a magazine company working with brands like Lexus and Microsoft, noticing the whole time that none of them ever thought about how they sounded. When he sold the company in 2002, he built an audio branding agency around that exact question.Years later, giving one of his five TED Talks, the real insight hit him: companies don't think about sound because they're full of people who don't listen. Research now puts the global cost of workplace disengagement from not listening at $8.8 trillion a year.He draws a hard line between hearing and listening. Hearing is passive. Listening takes four things: consciousness, commitment, compassion, and curiosity, and most people skip all four."The highest performing salespeople listen twice as much as they speak. The lowest performing salespeople speak twice as much as they listen."Julian also just launched his first app, Master Conscious Communication. Our audience gets 20% off the first payment!

    Do Hard Things A Podcast With Gabe Lullo Ft. Julian Treasure

  6. Sep 21

    Do Hard Things A Podcast With Gabe Lullo Ft. Ryan Frey

    "Everything we do as entrepreneurs is risk. But you can take educated guesses and educate yourself on how to do it." - Ryan Frey Ryan started his career in the Peace Corps, building rural water systems in Bolivia, barely speaking the language and with no money to do it.  In two and a half years, he finished one project.  What he actually learned wasn't construction, it was how to find funding, design something from nothing, and grind projects out no matter how long they take. He brought that grinder mentality into 25 years of real estate development in Missoula, Montana: infill housing, multifamily, industrial, large-scale residential, whatever deals came his way in a market of 120,000 people.  He recently entitled a 300-unit build-to-rent project and sold it rather than building it out himself, a decision he credits less to strategy and more to staying unattached to any single project and taking the right offer when it came. Now he's focused on solving Montana's housing affordability gap with factory-built homes, 20-30% cheaper than stick-built construction, targeting the growing space between renters and first-time buyers priced out by the state's post-COVID, post-"Yellowstone effect" boom.  He's walked away from deals that looked perfect on paper over a single detail, like insufficient parking, that would have broken the project regardless of the numbers. "Most of us, it's easy to create the vision and then just not take action. My advice: get in there and grind it out. You'll get it done."

    Do Hard Things A Podcast With Gabe Lullo Ft. Ryan Frey

  7. Sep 16

    Do Hard Things A Podcast With Gabe Lullo Ft. Brooke Leone Shipman

    "The day I finally stopped pretending was the day I realized I wasn't performing anymore. I was just surviving. And that wasn't something I was willing to keep calling success." - Brooke Leone Shipman, Founder of CEO Woman Brooke was the first in her family to graduate college, raised without much structure but with a lot of drive. As a sophomore in high school, after being screamed at on the drive to school, she looked in the mirror and decided she got to choose who she was, not her environment.  That decision carried her from straight A's to a scholarship to a climb from executive assistant to chief of staff at one of the largest fintech companies in the world. For eight years, she was trusted with everything behind the scenes and invisible in front of it.  "So lonely, and also incredibly formative," she calls it.  Underneath the climb, she was performing a persona at work that clashed with who she actually was, telling herself she was fine for longer than she'd like to admit, because stopping meant admitting something wasn't working. A close friend saw something in her before she saw it herself, and kept following up: what are your next steps, what do you need.  That's what cracked open a door she couldn't close.  She left her senior role with no outside capital and built CEO Woman, a personal growth platform for ambitious women, deliberately positioned as a luxury brand, not for the price point, but for the standard of women in the room. "Redefining success never means asking less of yourself. It means getting honest about which standards are actually yours, and which ones were handed to you by someone else's agenda."

    Do Hard Things A Podcast With Gabe Lullo Ft. Brooke Leone Shipman

  8. Sep 14

    Do Hard Things A Podcast With Gabe Lullo Ft. Kyle Lucey

    “Failure was never really an option, nor was it accepted.” -  Kyle Lucey When Kyle entered financial advising in 2012, the odds were not exactly in his favor.  Roughly 89% of new advisors wash out within the first few years. From day one, the expectation was simple: work. Half-days, five days a week. Six to eight hours on weekends. Keep going until you built a successful practice. And despite joining his father’s business, Kyle didn’t get an easier path. He got a higher standard. His father told him it would take six to eight years to develop the technical proficiency needed to truly master the business. Kyle initially took that personally. Eventually, he realized his father was right. That same philosophy now shapes how Kyle works with his own clients. He doesn’t start the first meeting by talking about investments. He starts by getting to know the person. Are they a good fit? Can he serve them well? Can they build a relationship based on trust? He even refuses referral business from the CPAs and attorneys he sends his clients to, a decision that once left a CPA firm asking: “What’s the catch?” There wasn’t one. For Kyle, the business is ultimately about service, relationships, discipline, and doing what’s right for the client, even when there’s a short-term cost. And his advice to anyone thinking about their financial future? “Don’t wait.” You don’t need millions saved to start planning. You don’t need to have everything figured out. You just need to start making the right decisions early.

    Do Hard Things A Podcast With Gabe Lullo Ft. Kyle Lucey
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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
    118
  • Rating
    Clean
  • Copyright
    © Gabe Lullo
  • Show Website
    Do Hard Things Podcast