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Explore every episode of the podcast Do Hard Things Podcast

Dive into the complete episode list for Do Hard Things Podcast. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.

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TitlePub. DateDuration
Do Hard Things A Podcast With Gabe Lullo Ft. Julian Treasure23 Sep 202600:46:10

"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 Expert


Julian'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. Ryan Frey21 Sep 202600:25:57

"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 Podcast With Gabe Lullo Ft. Brooke Leone Shipman16 Sep 202600:25:49

"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. Kyle Lucey14 Sep 202600:46:44

“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. David Robinson09 Sep 202600:39:45

"Every business owner takes all this advice from bigger companies to grow, but when it comes to technology, they suddenly think they know better and try to do it themselves." - David Robinson, Founder of Stratos


David’s career started as a lighting technician for concerts featuring Katy Perry, Tiesto, Jay-Z and others.


Then unexpected fatherhood pushed him into "a real job."


A family connection brought him into healthcare technology, where he helped build one of the first electronic medical record systems for reproductive endocrinology.


The catch?


He’d never done anything like it before.


So he figured it out through weeks of sleepless nights.


Then came a chance conversation at a pool bar in Palm Springs.


David approached WebMD’s former CFO and somehow knew enough about his struggling company to get his attention.


That conversation led to a job offer in New York, and eventually to working alongside the Big Four consulting firms.


That experience became the blueprint for Stratos:


Take the technology, expertise, and infrastructure that Fortune 500 companies spend millions on, and make it accessible to the mid-market businesses that are often overlooked.


David has a pretty blunt take on those businesses.


They'll follow proven advice from bigger companies when it comes to banking, sales, hiring, and structure.


Then they get to technology and think:


“This is the one area I can figure out myself.”


So they hand it to a nephew.


So they hand it to a nephew, a freelancer, someone "good with computers." A few years later, they're paying for that decision.


David’s filter for business is simple:


“If we’re not helping you make money or save money, it’s probably not a good thing to be involved in.”


His view on AI is just as pragmatic.


Vibe coding isn’t going away.


But it can’t vibe-code compliance.


Deploying an AI-built tool without a technical partner behind it is rolling the dice, and for most regulated companies, that’s a bet they can’t afford to make.



Do Hard Things A Podcast With Gabe Lullo Ft. Anne Freedman08 Sep 202600:33:29

"Whenever you're doing a speech or a presentation, you've got to say the lines out loud as you're doing it. If you wait till you're all done, you're going to have twice as much work." - Anne Freedman


Anne started as a journalist before becoming a speaking coach, and assumed a speech was a speech, until an early client bombed a presentation she'd written for him. 


It read perfectly on the page. Out loud, from him, it was a disaster. 


That's when she realized writing for the eyes and writing for the mouth aren't the same skill at all.


She founded Speak Out in 1990 and has spent thirty-five years since working with people who are wildly accomplished by every measure and still terrified to stand up and talk. 


She doesn't treat that fear as a character flaw, she treats it as a skill gap: structuring the content, controlling your body and voice while delivering it, and being ready for the law of averages, because the mic will cut out or the coffee will spill eventually.


Her practice method cuts against instinct: rehearse a speech out of order, closing first, then opening, then the middle. 


Only in the last few run-throughs do you go start to finish, timed. 


And she's blunt about what separates people who break through from those who avoid the podium their whole career: they actually rehearse instead of trusting decades of expertise to carry them through unprepared.


"Keeping all this knowledge to yourself instead of sharing it is being selfish."



Do Hard Things A Podcast With Gabe Lullo Ft. Jeremy Levine02 Sep 202600:32:02

"Stop talking about AI. Start talking about value. This is our product, this is the value we drive, and if you want to understand how we do it, we'll show you.” - Jeremy Levine


Jeremy's career didn't start in sales, it started in art school, which teaches you everything except how to make money as an artist. 


He waited tables, moved to Israel, and worked call centers just to survive before finally breaking into tech. 


At 41, he applied to every SDR, AE, and CSM role he could find and got exactly one callback: WalkMe. 


Even that turned into a rejection email, "looking for somebody a little more junior." 


He wrote back one line, signed off "forever young at heart" with a winky emoji. 


Ten minutes later, he had a contract.


That decision kicked off five years at WalkMe during hypergrowth and an IPO, where he built outbound motions that landed logos like United Airlines, Walmart, and Home Depot.


He was eventually named one of Sales Hacker’s Top 50 sales professionals in the world.


Now, as CRO at an AI marketing technology company, he's blunt about the noise in his own category: every SaaS company has bolted AI onto its pitch, and almost none of them sound different because of it. 


His answer isn't to out-hype the market, it's to stop competing on the buzzword and talk about what the product actually does. 


He's candid that most AI messaging is aimed at investors, not customers, and confusing the two is exactly how companies end up sounding like everyone else.


"Nobody's cutting through by out-AI-ing the next guy. You cut through by going back to the product and the value."



Do Hard Things A Podcast With Gabe Lullo Ft. Josh Gratsch31 Aug 202600:37:37

"You cannot lead someone beyond the parts of yourself you refuse to look at." - Josh Gratsch 


Josh joined Ascend Innovations in 2016 as a data scientist, no leadership training, no formal path. 


When the company's original business model failed within its first two years, he stepped into strategy and operations simply because he was willing to take initiative. 


Six years later, he was CEO, promoted by leaders who saw a capability in him he hadn't yet connected to himself.


Then reality hit. 


He'd spent his whole 20s chasing the title, achieved it, and felt nothing. 


Within the first six months, a spinout company he chaired collapsed and a business development process he'd trusted without accountability measures turned into a cash flow crisis that cost three leadership team members their jobs.


"I told myself the most effective leaders are optimistic. What I quickly understood was I didn't balance the equation. Hope is not a strategy."


The real shift came from turning the lens inward, tracing his default reactions, defensiveness, control dressed up as ownership, back to where they actually came from. 


He noticed the gap first at home, wondering why he could stay curious with his team but lose patience with his own kids.


That work reshaped how he leads now. 


Setting direction but actively inviting his team to tell him when he's wrong, because a team that can't have honest conflict can't truly commit to anything together.



Do Hard Things A Podcast With Gabe Lullo Ft. Vel Johnson26 Aug 202600:36:15

"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. Michael Hanson24 Aug 202600:31:54

"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. Marc Anthony Longwith19 Aug 202600:31:59

"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. Ryan O'Hara17 Aug 202600:37:56

"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. Michael Assraf12 Aug 202600:41:12

"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. Yaron Vorona10 Aug 202600:32:24

"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. Stephen Klein06 Aug 202601:01:18

"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. Vahid Fakhr04 Aug 202600:34:47

"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. Evin Schwartz29 Jul 202600:43:47

"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. Ned and Jamie Arick28 Jul 202600:53:02

"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. Joey GIlkey22 Jul 202600:41:59

"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. Robin Dimond20 Jul 202600:28:45

"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."



Do Hard Things A Podcast With Gabe Lullo Ft. Dean Harrison15 Jul 202600:32:20

"I slept with my snorkel gear every night. I thought I was going to have to swim my way out when the boat capsized." - Dean Harrison, The Yacht Chef


Dean started at 15, chopping parsley for five hours while chefs laughed at him from the back door. 


He was physically assaulted in that first kitchen, called his mom crying, and quit. 


A second restaurant with real mentors brought him back and reminded him why he loved cooking in the first place.


At 18 he bought a one-way ticket to Europe, ran out of money in the French Alps, and stumbled into a conversation with a yacht chef who spent every winter off because the summer pay was so good. 


That was all he needed to hear. 


The decade that followed is hard to summarize. 


He survived a six-day South Pacific storm where two people on other boats died and the stabilizers failed on his. 


He was held at gunpoint by Libyan armed forces for ten hours before the embassies got involved and they finally let the crew go.


He came out the other side of both and kept sailing.


His take: when else would a chef get to do any of this? 


The hard moments are the ones he looks back on most, and the reason he started documenting everything, to show the next generation of yacht chefs what the job actually looks like, not just the glamour, but the storms and everything in between.


"I don't chase jobs for the money. I chase them for the experience and for where they take me."

Do Hard Things A Podcast With Gabe Lullo Ft. Leslie Venetz13 Jul 202600:41:09

"Most sales teams don't have a tactics problem. They have a trust problem. For decades, we have taught our buyers to not trust us." - Leslie Venetz, Founder of Sales-Led GTM and USA Today Bestselling Author


Leslie was on track to become a CRO by 40. 


The offer was on the table: $460,000. 


She turned it down the same day, walked away from the goal she'd spent her entire career building toward, and paid herself $50,000 in year one of her own business.


The philosophy behind her agency came from a mistake she made early. 


Six months into her first corporate job, her manager got fired and she inherited a team ten years her senior.


She assumed the title came with trust. It didn't. 


From that experience she built what she now calls the earn the right framework: before you do anything, ask yourself whether you've actually earned the right to ask for this person's attention.


Most teams skip that question entirely, which is why their pipeline looks like a tactics problem but is really a trust problem.


On curiosity, she doesn't accept "I'm just not naturally curious" as an answer. 


If someone told you that you needed a 50% free throw percentage, you'd know immediately the path there was practice. 


Curiosity works the same way.


"Grit isn't doing one hard thing for two weeks. It's showing up for months and years toward a bigger purpose, even when it doesn't feel like it's working."



Do Hard Things A Podcast With Gabe Lullo Ft. Paul Higgins08 Jul 202600:34:59

"I did a reverse image search, found his wife's bakery in Illinois, and put in an order for cakes with a note inside. He called me at 6:30 the next morning." - Paul Higgins


Paul's sales career started on an ice cream van.


Before that, he was upselling cologne to classmates at school for 50p a spray.


He talked his way out of a post room job after hearing the buzz of the call center floor and deciding that's where he belonged.


From there, it was pensions, then insurance, then recruitment tech, teaching himself HTML and CSS along the way.


A mentor once handed him two VHS tapes: Boiler Room and Glengarry Glen Ross.


He says they changed his career, cutting his daily call volume from 150 dials to just 40 because they taught him something volume never could: how to actually close.


What sets Paul apart today is his ability to sit with a CTO and talk architecture, then walk into the CFO's office and talk about cost savings that same afternoon.


Most reps only speak one language. He learned to translate between technical and commercial conversations by understanding how the products actually worked, not just how to pitch them.


That same mindset shows up in his prospecting.


One unicorn account had gatekeepers he couldn't get past for months.


So he reverse image searched the decision-maker, found his wife's bakery in Illinois, ordered a box of cakes, and tucked in a handwritten note asking for a callback.


It worked.


That single conversation became a five-year, $1.2 million contract.


His research is just as methodical.


Before his team calls a prospect, they already know how many job boards the company uses, how many developers they employ, and roughly what their current setup is costing them.


That level of preparation helped improve SQL-to-close rates by 40%.


Not by making more calls.


By making smarter ones.


"Don't dwell on the things you messed up on. I've lost millions. The more you put in, the more you get out."



Do Hard Things A Podcast With Gabe Lullo Ft. Malisa Nguyen07 Jul 202600:43:08

"If you're operating in survival mode, that's when it leads to burnout. That's when it leads to the rock bottom moments that a lot of reps struggle with." - Malisa Nguyen, Mental Performance Coach and Founder of MTN Collective


Malisa went from top performer to burning out in a role she earned through a promotion she worked hard to get. 


She did everything sales culture told her to do: more volume, more hustle, longer hours. 


She worked weekends and twelve-hour days and still couldn't find her footing. The pressure gave her anxiety attacks at night and made her unable to be present in her own life. 


She went to an Anderson .Paak concert and spent the whole time thinking about quota.


That experience sent her down five years of studying mental performance and nervous system science, and what she found reframed everything she thought she knew about sales inconsistency.


Her core argument: inconsistency isn't a skill problem. It's a nervous system problem. 


Spraying and praying is a fight response. Procrastinating on cold calls is flight. Freezing in analysis paralysis is exactly that. Over-discounting to please a prospect is a fawn response. 


None of those are fixed by more roleplay or more pressure. 


In fact, piling on pressure usually makes all of them worse.


The reps who bounce back from rejection quickly aren't tougher. 


They've just stopped making it mean something about themselves. 


The moment you tie the outcome to your self-worth, the spiral starts.


"You can only go so far hustling and grinding your way through. Eventually you're going to hit a wall. I hit that wall."



Do Hard Things A Podcast With Gabe Lullo Ft. John Melton02 Jul 202600:43:14

"You can't just follow up with someone when you have an agenda. Staying in touch with people without even talking about your product is probably one of the most impactful things you can do." - John Melton, Marketing Veteran and Entrepreneur


John started out as a kid who hated school, was getting into fights, and had no direction. 


Two weeks before 9/11, a friend brought him to a marketing presentation. He thought it was a genius idea. But the company eventually got shut down, but what he learned there became the foundation for everything that followed.


He took those skills into mortgage sales, made real money for the first time, and eventually came back to network marketing when social media arrived and changed everything. 


His organization has done $450 million over the last decade. He calls it a 16-year overnight success story.


What separates the people who make it from those who don't, in his experience, has nothing to do with talent. 


It's coachability. 


On content, the formula is simple: be entertaining, empowering, or educational, and don't be boring. The algorithm doesn't care how many followers you have.


But the principle he keeps coming back to, the one he's built 25 years on, is follow-up. 


Not an aggressive follow-up. Just staying in touch. Wishing people a happy birthday. Sending a voice note. Checking in without an agenda. 


People who had been watching from the sidelines for years finally reached out when the timing was right, because the relationship was already there.


"The fortune's in the follow-up. Be a friend first and a marketer second. It's amazing what you attract."



Do Hard Things A Podcast With Gabe Lullo Ft. Tony Brophy29 Jun 202600:24:41

"People don't actually do the thing for hours on end every day consistently. They just talk about theory." - Tony Brophy


Tony started cold calling in a boiler room in Dublin. His first day on the job, someone handed him a phone, a stack of magazines, and a script, then told him to start dialing. 


He had no idea what he was doing, but he kept showing up anyway, and two years later he built a business around it.


Not a coaching program. Not a course. Actual cold calling, for clients who hand him a list and expect results. 


Six hours on the phone the day he recorded this episode, running hour-and-a-half call blocks five or six times a day, speaking to roughly 20 people per block, a quarter of whom hang up the moment he opens his mouth.


He calls it getting kicked in the teeth for a living.


The reason he went all in on one channel and one service, no multi-channel strategy, no fancy funnels, is simple: he's got ADHD and if he doesn't lock onto one thing, he goes off the rails. 


So he picked the hardest thing in sales and did it every single day until the discomfort became background noise.


His advice to new SDRs comes down to a few things. 


Set call blocks and protect them. Follow the script instead of trying to be clever before you've earned the right to improvise. Speak like a normal person, not like someone auditioning for a movie.


And when a prospect asks if you're AI, have something ready. His line: they don't have the Irish accent on AI yet, mate.


Everything else is just showing up and making the dials.


"The only way you're going to get better is by pushing through that fear and that discomfort. Nobody else is going to do it for you."

Do Hard Things A Podcast With Gabe Lullo Ft. Neil Weitzman24 Jun 202600:42:33

"The GTM bar is quite low. And that's a good thing for those of us who get it." - Neil Weitzman, Fractional CRO and Founder of Weitzman Go to Market


Neil's philosophy comes down to three words: get it done.


Not more frameworks, not more slide decks, just execution.


His take on the say-do ratio is simple:


If you say you're going to do something, do it.


If you can't, communicate it before someone has to ask.


Sounds obvious. Yet most companies still miss the mark.


The follow-up that never comes, the quote promised on Tuesday that's still sitting in the drafts on Friday. The proposal that takes two weeks instead of two days.


Neil's point: the bar is so low that simply doing what you say you'll do already puts you ahead of most of the market.


When he joins a company as a Fractional CRO, he starts with the data.


Do they know what good looks like in their funnel?


What's converting? Where are deals getting stuck?


Most companies have fragments of the answer. 


Very few use that information to coach, hire, and improve consistently.


Build the foundation, create repeatable systems, get the team running, and eventually hand it off to a full-time leader.


And for founders who say they want honest feedback?


He'll give it.


The best ones are willing to hear it.



Do Hard Things A Podcast With Gabe Lullo Ft. Sam Hollander22 Jun 202600:36:48

"You still have to have some form of human personalization. You still have to pick up the phone. You still have to build relationships." - Sam Hollander


That's Sam Hollander's view on AI in sales.


Not because he's anti-AI. Quite the opposite.


After 18 years building revenue in markets where the traditional playbook doesn't exist, he's seen firsthand where technology helps and where it doesn't.


He's led two companies through successful exits, and his first 90 days always look the same: talk to customers, pressure-test the messaging, and build operating structure.


Because in startups, ambiguity is the biggest challenge. The only way through it is to create your own anchor.


When it comes to outbound, Sam doesn't think the answer is more automation.


At a conference last month, he watched a friend open her inbox:


1,000 unread emails from vendors.


Just sitting there.


That's why he's building LynkUp, a marketplace that connects high-intent buyers and sellers at conferences, turning random badge scans into intentional, confirmed meetings.


The biggest deals of his career didn't start in an email sequence. They started in person.


His advice for enterprise sales is simple: map stakeholders early, identify champions and blockers, and stay in touch consistently. Momentum matters.


AI is great for saving time. 


Great for research, writing, and prep work.


But relationships still close deals.



Do Hard Things A Podcast With Gabe Lullo Ft. Zack Schneider17 Jun 202600:27:01

"Do you have the grit necessary to see it through? That's where I see a lot of people struggle." - Zack Schneider, Founder of Agency 15


Zack started his first agency at 19. Not because he had a plan, but because he had nothing to lose. By 26, he had scaled it to an exit.


He'll be the first to tell you that naivety was the advantage.


At Agency 15, every team member keeps a carabiner on their desk with 30 fundamentals on it. 


Not values. Fundamentals. Specific, observable behaviors that managers can coach in real time.


One fundamental each day. Every day.


Until they stop being reminders and become habits.


Today's fundamental: Practice blameless problem solving.


Apply your creativity to solutions, not finger-pointing.


Learn from mistakes faster than everyone else.


Simple doesn't mean easy.


In fact, most of the things that actually work are surprisingly simple.


The biggest leadership lesson Zack learned came later.


Growing the company wasn't about strategy.


It was about replacing himself, over and over again, with people who were better than him at the things he used to do.


He compares it to mountain climbing.


As the altitude changes, some people adapt and keep climbing with you.


Others reach a level where they can't go any higher.


That doesn't diminish what they contributed.


It just means they aren't the right people for the next stage of the climb.


The companies that succeed aren't built by people who never struggle.


They're built by people with the grit to keep climbing anyway.



Do Hard Things A Podcast With Gabe Lullo Ft. Tom Farley15 Jun 202600:49:21

"We tell our stories because we do not heal in isolation. We need each other." - Tom Farley, Recovery.com


Tom will tell you upfront that he doesn't walk into a room to motivate anyone. 


He walks in because he needs to be there just as much as the person sitting across from him.


He grew up in a big Irish family in Madison, Wisconsin, where drinking was just how you handled anything uncomfortable. 


By the time he got to Georgetown, then Wall Street, he had built an entire identity around being sharp, polished, and put together, with no idea how hollow it felt underneath.


The moment that cracked something open came before his own recovery. 


He went to an AA meeting with his brother Chris Farley, in a basement in Hell's Kitchen, and watched him stand up and be more honest than Tom had ever seen him, in front of a room full of strangers. 


He didn't understand it yet. But he never forgot it.


Years later, when he found his own way into recovery, he finally did. 


The only place he has ever felt real belonging wasn't his family, his career, or his religion. It was a church basement with people he never would have thought to sit with otherwise.


He's been to recovery centers, prison programs, veterans' groups, and boardrooms since. 


What he keeps finding is the same thing: people don't lack the desire to get better. They lack permission to be honest about where they actually are.


His take on stigma is simple. 


It comes from fear, and the only way through it is real human connection, not awareness campaigns, not likes or shares, but someone looking you in the eye and saying, I've been there too.


"Recovery exists on the other side of fear. Every time you walk through it instead of drinking it away, you get stronger."



Do Hard Things A Podcast With Gabe Lullo Ft. Brianne Price10 Jun 202600:27:37

"The brand is the most important thing. Everything you put out into the universe has to align with your three pillars. And if it doesn't serve you, cut bait and move on." - Brianne Price, CPG Executive and Chief Revenue Officer


Brianne didn't get into consumer brands from a business school case study.


She got in from a salon floor, sweeping hair, when a new line called Bumble and Bumble came in and she thought the packaging and messaging was the coolest thing she'd ever seen.


That moment launched a career scaling brands from under $10 million to over $100 million.


The hard part was never the product.


It was knowing when to stop protecting what was built and start being honest about what needed to change.


Her take on where most brands get stuck: they get really good at one channel, Amazon, DTC, or retail, and struggle to make the jump to the next.


The brands that break through aren't necessarily the ones with the best product. Everyone has good products now.


What separates them is whether consumers see the brand as part of their lifestyle, not just something on a shelf.


Her advice to founders stuck between $5 million and $20 million comes down to one question:


What is your customer's experience like right now?


The longer you're in business, the easier it is to see your brand through internal eyes instead of customer eyes.


That's when growth stalls.


The brands that reach the next level are willing to challenge their assumptions, stay aligned with what the brand stands for, and adapt before the market forces them to.


They stay honest about what's working, what's not, and what needs to change.



Do Hard Things A Podcast With Gabe Lullo Ft. Ari Barmapov08 Jun 202600:34:40

"A lobster knows when it's time to shed its shell when it starts getting uncomfortable. If it never felt uncomfortable, it would never grow." - Ari Barmapov, Co-founder of Foundations


Ari didn't start in a boardroom. He started at Blockbuster, selling membership add-ons from behind a cash register, just asking everyone who walked in. 


The more he asked, the better he got, and he ended up the top salesperson in the entire district. 


That was the whole formula, and it hasn't changed since.


No auto-dialer, no real CRM. Just a phone, a phone book, and 150 to 200 manual dials a day. 


Brutal reps, but invaluable ones. 


Four President's Clubs later, he built Foundations to give founders what nobody gave him.


His take on why founders stay stuck in founder sales: they try to delegate before they've done the work themselves. 


BDRs aren't there to figure out your business, and a VP of Sales isn't going to cold call for you. 


The only way out of founder sales is through it. 


Do it yourself, do it a hundred times, know what works, then pass it on.


On cold calling being dead: it isn't. 


People say it's dead because you can't sell a $99 course on it. 


You actually have to pick up the phone, and most reps today won't sit down and make focused calls for 90 minutes.


Not because they don't have the time, but because they don't want to be uncomfortable. 


That discomfort is the whole point.


The one question he leaves every founder with: when was the last time you booked a meeting with someone you didn't know? 


If you can't remember, you already know what to do next.



Do Hard Things A Podcast With Gabe Lullo Ft. Chason Forehand03 Jun 202600:34:33

"We don't just flip eggs. We flip lives." - Chason Forehand, Founder of Transformation Kitchen


Chason is a HR advocate with 45 years spanning culinary, human resources, and DEI. 


He is someone who knows exactly what it feels like to need a sandwich and have no idea what comes next.


Chason grew up as the oldest of six boys in an abusive home. By college, the guardrails were off. Straight-A student to academic probation in under a year. Drugs. An attempt on his own life. Incarceration.


Then a chef found him. Ten years clean and sober, someone who cared as much about people as he did about food. He became a mentor, a sponsor, a friend. That changed everything.


The hardest thing Chason ever did wasn't build a program. It was putting his hand up and asking for help.


Now he makes it easier for others to do the same.


Transformation Kitchen isn't job training. It's what he calls a forge.


You come in, you transform, and you never age out. The metric isn't who completed the 12 weeks. It's where you are five years later. Still housed? Still employed? Still clean?


Because if all you hand someone is a sandwich, you've handled today. Nothing else.


"The most profitable companies are driven by purpose."


Doing hard things isn't just a personal challenge. It's an organizational one. 


It means paying people what they're actually worth. 


It means building culture that outlasts any one quarter. 


It means showing up for your community when there's no immediate ROI.


For companies that want to get involved beyond writing checks: volunteer, join a board, post about an organization you believe in. 


Your social circle is different from theirs. That difference has real value.


Start there.



Do Hard Things A Podcast With Gabe Lullo Ft. Julee Gracey01 Jun 202600:36:40

"People are just waiting for permission to go after their dreams. I never ask permission. If I want it, I go after it.” - Julee Gracey


Former international model, People magazine's 100 Most Beautiful, NBC's Deal or No Deal, Top real estate agent, and now a business coach who helps entrepreneurs stop hiding and start showing up.


She's been called human Red Bull and you'll understand why in about 30 seconds.


Julee grew up on a farm, worked construction, and then flipped through magazines one day and noticed all the models were traveling the world. 


So she became one. Not because she dreamed of runways, but because she wanted to see what was out there.


After a decade in LA, she came home and went into real estate. Everyone told her it was a terrible idea. 


She got quiet, went under the radar, and became the top agent in her office.


Her first showing was a disaster. She couldn't unlock the door, couldn't answer a single client question, and got fired on the front porch. 


She cried for a day, then walked up to the number one agent in the office and said: take 50% of everything I make. I just want to sit in your meetings and hear the words you use.


Within months she was posting the biggest numbers on the board. She's never tackled anything since without a mentor.


What she figured out that most people won't say out loud: burnout isn't from doing too much. It's from doing the wrong things. And most entrepreneurs struggle to talk about what they do because they were taught growing up to sit down, be quiet, don't brag. 


Then they start a business and every one of those rules becomes the obstacle.


Her fix: face the thing you're avoiding. That's exactly where your growth is.


She wrote it all down in Highly Confident, now a number one Amazon bestseller. The core message: get clear on what you want, make better decisions, and stop waiting for permission.


Nobody's coming with that slip.



Do Hard Things A Podcast With Gabe Lullo Ft. Larry Raskin27 May 202600:34:23

"When you open your mouth, the world will discover who you really are." - Larry Raskin


38-year veteran in sales and marketing, former VP of Leadership Development, and the man I credit to teaching me how to communicate and build businesses.


This one is personal.


Larry didn't start in sales, he started in pro baseball. 


An injury ended that, so he pivoted into the only world he knew: fitness. 


Managing health clubs through the fitness boom, 10 to 10, six days a week.


At some point the math became obvious. The harder he worked, the richer other people got. He was the engine with no equity.


So he answered a newspaper ad, walked into a strip mall meeting that looked nothing like the six-figure promise in the listing, and almost left. 


He stayed because he loved the concept, not the product. Business ownership with income that worked beyond his own effort.


And he never looked back.


Over the next 38 years became one of the most successful producers, sales trainers and leadership speakers in his company’s history. 


Then the pandemic hit and Larry went from the top of the mountain back to zero.


He didn't coast. He started over.


At 43, heart blockages. More stents in 2005. Bypass surgery at 66. Back in the gym after every single one.


"It isn't what happens to you. It's what happens in you that matters."


Now at Zinzino, a science-backed preventative health company built around test-based, personalized nutrition, he's more fired up than he's been in decades.


His philosophy hasn't changed in 38 years: your organization will never outgrow your personal development. 


Treat it like a business or don't. Find the voices worth emulating. Repeat until it sticks.



Do Hard Things A Podcast With Gabe Lullo Ft. Scilla Andreen20 May 202600:42:50

"We are so much stronger than we are ever told we are." - Scilla Andreen 


As an Emmy nominated costume designer, co-founder of IndieFlix, award-winning filmmaker, CEO of Impactful Networks, and Mother of six, Scilla knows what doing hard things is all about. 


She lost her son to suicide, and her daughter to cancer on her birthday. 


Three days after her son passed, she got on a plane to a conference on men's and boys' mental health. Not because she was okay, but because she had questions, and she refused to stop asking them.


It's who she is.


Long before any of that, a friend named Tina, the executive director of her foundation, kept asking her to make a film about mental health. She kept saying no… nobody wants to watch a movie about mental health.


Then Tina passed by suicide.


Scilla had no mental health background; she had grief, guilt and questions. 


She did the only thing she knew… started filming anyone who would talk to her, from Harvard researchers to six-year-olds, with no script and no money. 


That turned into her film, Angst. It sat for six months, then screened in 90 countries within 14 months.


The insight that drove all of it: the power of a film isn't in the watching, it's in the conversation after. 


When people feel safe enough to talk, they share what they've been carrying alone.


The mission isn't therapy, it's education. 


Mental health literacy is a population-level problem, and the solution looks more like CPR training than a clinical appointment. Everyone needs access.


Human connection matters more than ever right now. 



Do Hard Things A Podcast With Gabe Lullo Ft. Kade Hinkle18 May 202600:23:17

"You don't need to post something groundbreaking every time. Just post your story. People are going to like that because they can see themselves in you." - Kade Hinkle


Kade’s a young SDR in the game and he's been on LinkedIn longer than most sales reps you know.


Not because someone told him to. Because he watched a YouTube video at 16, figured out LinkedIn was where the jobs were, and started connecting with people before he ever graduated high school. 


By the time he did, he had 2,000 connections and a job offer waiting in his inbox.


He started in landscaping and now he's cold calling executives every afternoon and booking meetings from LinkedIn DMs in between, with over 12,000 followers.


He's not doing anything magical. Prospecting in the morning. Emails around noon. Calls from 3 to 5. 


Video messages when he remembers to push himself. Posts at the end of the day from whatever he wrote in his notes app.


The difference is he started. At 16. While most people his age were doom-scrolling Instagram.


The rejection question came up. How do you handle getting punched in the face all day as a brand new SDR?


His answer was pretty simple: "I know it's not personal. So you just keep moving to the next one."


No elaborate mental framework. No morning routine. Just the understanding that a no isn't about you, and the next call is waiting.


Here's what stuck with us though. Kade wants to be an AE by 20. After that it gets blurry. Maybe leadership. Maybe his own business. He's not sure yet.


But he knows one thing: he's not waiting until he has something impressive to say before he starts showing up. 


He's posting the journey in real time, figuring it out in public, and letting people grow with him.


In the age of AI, that's exactly what cuts through.



Do Hard Things A Podcast With Gabe Lullo Ft. Leo and Clarissa Martinez13 May 202600:54:09

"You're only going to go as far as your identity takes you." - Leo Martinez


Leo is the Co-founder of Martinez and Associates Consulting. 25 years in business with his wife Clarissa. A 21-year-old company that now runs 99% without them in it.


He didn't learn that in a classroom. He learned it after spending seven years inside Patrick Bet David's inner circle, having 15 to 18 conversations a day, six days a week, with founders and CEOs running companies from $2 million to $12 billion.


After all of that, the pattern was clear.


But before we get there, here's what actually built the foundation.


Leo is the dreamer. Big vision, moves fast, commits before he has all the answers. Clarissa is the one with 27 objections and 30 questions. She pumps the brakes. She asks what nobody wants to ask.


Her words: "You need two people that are almost opposites coming together in order to balance each other out."


That's not just their marriage. That's their entire operating model.


Most entrepreneurs live in the "if it is to be, it's up to me" trap. All the pressure on their shoulders, nobody empowered to carry any of it. The business grows to a point, then stops. Not because the market ran out. Because the founder's identity did.


Clarissa added what most people miss: founders think they're doing the right thing by pouring everything into the business. But while they're winning at work, they're quietly losing at home.


You don't have to pick one. But you do have to be intentional about both.


Their ops manager Diana has been with them 14 years. Not because of the salary. Because Leo and Clarissa invested in her life, not just her output.


"You have to love them. If you love them, they will go through walls for you."


That's not soft. That's the whole system.



Do Hard Things A Podcast With Gabe Lullo Ft. John Zurowski12 May 202600:27:41

"My success is actually when a client stops working with me." - John Zurowski  


John is the Founder of JZ Sales Consulting with Twenty years of corporate sales leadership before going fractional. And that line is the most honest thing you'll hear from a consultant this year.


His goal isn't to become indispensable. It's to build companies to the point where they can replace him with a full-time leader. He calls that the win.


Most founders hitting a growth ceiling make the same move: rush to hire a senior sales leader. Big salary, fancy title, high expectations. And more often than not, it doesn't work.


Not because the hire is wrong. Because the foundation isn't there yet.


John sees it constantly. You sit down with a company's employees and ask a simple question: what does your company do and what problem does it solve?


You'll get five different answers. Every time.


If your own team can't align on that, no sales leader in the world is going to fix your pipeline.


That's where John starts. Not with a CRM. Not with a headcount plan. With clarity.


Get the team aligned on what you do and who you help. Build process that's designed to flex, not break. And when you're stuck, stop looking for a new tactic. Go back to the fundamentals.


He put it simply: "When you're in a rut, it just takes one small win to get that wind in your sail again."


Make the extra calls. Review your proposal with fresh eyes. Do the basic things well. The breakthrough rarely comes from doing something new. It comes from doing the right things consistently.


John's also direct about AI: it's a productivity tool, not a replacement for genuine human conversations. People still buy from people. That hasn't changed, and the market fatigue with AI-driven outreach is only going to accelerate it.


The sales leaders winning right now are the ones combining structure with hustle, and knowing the difference between a phase and a ceiling.



Do Hard Things A Podcast With Gabe Lullo Ft. Pierce Brehm06 May 202600:29:08

"If it's not producing pipeline, it's not a partnership. It's a coffee club." - Pierce Brehm 


Pierce is the Founder and CEO of Holland Lane Global Advisers. And if you've ever announced a new logo, signed an agreement, done a webinar, and wondered why none of it turned into revenue, this ones for you. 


Most companies know partnerships should be part of their growth strategy and the data backs it up. 


Deals close 53% more often when a partner is involved and close 46% faster. 


A recommendation from a trusted source is up to 50 times more likely to result in a purchase than a cold outreach.


So why do so many partnerships go nowhere?


Pierce has a simple answer, there is no ideal partner profile, no activation plan, no shared revenue target, and no measurement. 


Companies are treating partnerships like a branding exercise instead of a revenue channel.


Pierce's framework starts at the foundation: define your ideal partner profile. 


Who's selling to the same types of companies, the same personas, the same industries? 


Who compliments you without competing? Get that right first. Everything else builds from it.


Then comes consistency. Not a logo swap and a LinkedIn post. Consistent communication, proactive introductions, and a clear way to track what's actually converting.


When you get it right, partnerships stop feeling slow and unpredictable. They become one of the most efficient growth channels in B2B.


The companies winning right now aren't making more noise. They're building stronger relationships, on purpose, with a plan.



Do Hard Things A Podcast With Gabe Lullo Ft. Gabe Naviasky04 May 202600:35:02

“AI is just an extension of software. It essentially makes what we have been doing much better.” - Gabe Naviasky


In this episode, Gabe shares a story about a company that chose not to work with his team simply because they were using AI.


At first glance, it sounds cautious and even reasonable. This company had experienced a security breach the year before, so their hesitation around vendors like OpenAI made sense.


But here’s the part that’s harder to reconcile:


Avoiding a specific vendor is one thing. Avoiding AI altogether? That’s a different story.


Because opting out of AI today doesn’t just mean skipping a tool, it means stepping away from the infrastructure of modern software itself.


It means:

• No Google search

• No Siri or voice assistants

• No smart automation quietly improving workflows in the background


AI isn’t a feature anymore, it’s becoming the baseline.


As workflows become more automated, the nature of work itself is changing. The repetitive, manual, and process-heavy tasks? Those are increasingly handled by systems.


What’s left, and what becomes more valuable, is the work that requires judgment, creativity, and real-world experience.


The human layer doesn’t disappear, it sharpens.


So the question isn’t whether to use AI.


It’s how intentionally we choose to use it and where we decide human expertise matters most.



Do Hard Things A Podcast With Gabe Lullo Ft. Karen Laos29 Apr 202600:41:00

“We all have agency to speak up, and it’s incredibly liberating.” - Karen Laos


Karen came to this realization after a moment that could have easily been dismissed as just another bad day at work.


She was in a boardroom giving a presentation when she suddenly froze. Instead of pushing through, her boss stopped the meeting. 


Later, she pulled her aside and asked a simple but powerful question: why didn’t you just table the discussion, and why do you keep asking for permission?


That question stayed with her.


As she reflected, Karen recognized something deeper, she didn’t actually agree with what she had been presenting. 


But she had been raised to respect authority, not challenge it, and certainly not push back in a room like that.


In that moment, she saw how much she had been holding herself back.


What started as an uncomfortable experience became a turning point. 


It led her to rethink how often people stay quiet, even when they have something important to say, and ultimately inspired her to help others find the confidence to use their voice.


It’s easy to stay silent, especially when speaking up feels risky. But over time, that silence can become a kind of prison we create for ourselves.


Speaking up isn’t about being difficult or confrontational, it’s about being honest and bringing your full perspective to the table.


If something doesn’t sit right with you, it’s worth saying so.


You’re in the room for a reason, and your voice carries more value than you might think.



Do Hard Things A Podcast With Gabe Lullo Ft. Matthew Beaudin27 Apr 202600:41:25

“You need to get comfortable with you. You are the reason you are going to fail. You are the reason you are going to succeed.” - Matthew Beaudin


It’s easy to point fingers to market conditions, pricing, competition, or timing when things don’t go our way. 


But the truth is, the biggest variable in any outcome is us.


Our mindset.


Our consistency.


Our willingness to have uncomfortable conversations.


Our discipline to follow up when others don’t.


The same is true on the flip side.


The wins? They come from preparation no one sees. 


From resilience after rejection. 


From choosing to improve instead of making excuses.


If you’re in sales right now, here’s the real question:


Are your daily habits aligned with the results you say you want?


Because growth in this field doesn’t start with a new script or tool, it starts with ownership.


And when you fully own your outcomes, everything changes.



Do Hard Things A Podcast With Gabe Lullo Ft. James Bissell22 Apr 202600:46:46

“Get out there and make it happen. Don’t sit back and wait for it to come to you, it probably never will, not in the time you want it to.” - James Bissell 


Success in sales isn’t something that just shows up at your door.


Nothing is handed to you in this game. 


No shortcuts, no easy wins.


It takes grit. 


It takes consistency. 


It takes showing up even when you don’t feel like it.


And above all, it takes action.


You can’t afford to be lazy and expect results. 


The people who win are the ones who go after it, every single day.


Go make it happen.



Do Hard Things A Podcast With Gabe Lullo Ft. Teegan Bartos20 Apr 202600:42:04

“When you’re competing at the executive level, everyone is qualified. What separates you is who you genuinely are.” - Teegan Bartos


Your network is your net worth, but only if people truly understand who you are and what you stand for.


It’s no longer enough to look good on paper.


Titles, resumes, and credentials may open doors, but they don’t build trust or lasting influence.


Legacy is built through visibility and authenticity.


Share your journey.


Show your impact.


Let people see the results you’re driving.


Not just within your organization, but in the broader community around you.


Because if people can’t see what you’re building, they can’t be part of it.


And if they can’t understand your value, they can’t advocate for it.


Your brand isn’t what you say it is, it’s what others consistently experience and recognize.


Make it visible. Make it real.



Do Hard Things A Podcast With Gabe Lullo Ft. Justin Zelik 16 Apr 202600:30:39

“There is so much opportunity in B2B for content.” - Justin Zelik


LinkedIn has changed the game.


Years ago, LinkedIn was just a place to find a job.


If you weren’t hiring or job hunting, you barely logged in.


Now? We’re on it every day.


Not just to prospect.


Not just to network.


But to build.


To build personal brands.


To build trust at scale.


To build relationships before a single call ever happens.


The biggest shift isn’t the platform, it’s the behavior.


Buyers don’t want cold pitches.


They want context.


They want credibility.


They want to feel like they already know you before you reach out.


And content is how you get there.


In B2B, attention used to be rented (ads, outbound, events).


Now it can be owned.


The people consistently showing up, sharing insights, documenting their thinking, they’re the ones winning long before deals are on the table.


If you’re in B2B and not creating, you’re invisible.


If you are creating, you’re compounding.


The opportunity isn’t coming.


It’s already here.



Do Hard Things A Podcast With Gabe Lullo Ft. Katy Rey13 Apr 202600:27:40

“Choose your hard. You can do hard things.” - Katy Rey


You are selling in every part of your life.


Not just at work, but in your relationships, your energy, and how you show up daily.


You’re selling:


Your character


Your consistency


Your belief


Every interaction builds trust or breaks it.


Because at the end of the day, connection is what wins.


People don’t buy into ideas, they buy into people.


And strong teams aren’t just talented, they’re connected.


It will get hard. That’s guaranteed.


So choose your hard:


Growth or staying stuck


Discipline or regret


Connection or distance


Choose the one that builds something real.



Do Hard Things A Podcast With Gabe Lullo Ft. Laura Skinner08 Apr 202600:34:49

“I would rather have so much pipeline and my deal acquisition be lower and some will have to drop, but I keep the pipeline going so that it is almost impossible to fail.” - Laura Skinner


This is what most people miss about cold outreach:


They chase perfection… the perfect script, timing, or lead.


But pipeline isn’t built on perfection. 


It’s built on volume and consistency.


Cold outreach is a reps game.


At first, it feels uncomfortable. 


You overthink, hesitate, and doubt if it’s working.


But if you get obsessed and put the reps in, everything changes.


You spot patterns. Your messaging improves. Your confidence grows.


And rejection stops mattering because your pipeline is full.


The goal isn’t to close every deal.


It’s to create so many opportunities that success becomes inevitable.


Volume beats perfection. Reps beat everything.


Keep the pipeline full and it becomes almost impossible to fail.



Do Hard Things A Podcast With Gabe Lullo Ft. Jonathan Gryzbowski06 Apr 202600:34:55

“You have to build the right systems in order to insure that you are profitable. And if you don’t have a good system you will fail. And if you don’t solve a problem, you will also fail.” - Jonathan Gryzbowski


It’s easy to focus on big ideas, but long-term success often comes down to two things:


→ Solving a real, meaningful problem


→ Building systems that consistently deliver that solution


When those two pieces are in place, things tend to run more smoothly.


You gain clarity, consistency, and a clearer path to growth.


And when something feels off, it can be a helpful signal:


Maybe the problem needs to be better defined, or the system needs a bit more structure and refinement.


A simple check-in:


What problem am I solving?


What systems help me deliver value consistently?


Small improvements in either area can make a big difference over time.



Do Hard Things A Podcast With Gabe Lullo Ft. David Meltzer01 Apr 202600:46:03

“I want to provide content in two different ways. The authentic content that is aligned with my brand, and content that expresses my essence.” - David Meltzer


That’s how David thinks about it.


And once you hear him break it down, you realize, it’s not about posting more. 


It’s about being intentional.


Start with content that’s real. 


Not manufactured. Not forced. 


Just you, at your core.


Then shape it for the platforms. 


Same message, different packaging.


Then amplify it. Leverage the network, expand the reach.


And finally, build a place where it all lives. 


A social silo. Somewhere people can go deeper.


Because when it resonates… they don’t just like it. 


They lean in. They explore. They stay.


Billions of people don’t know who he is.


But to millions, it feels like he’s everywhere.


That’s not luck. That’s strategy.



© My Podcast Data · Independent project · Data from Apple & Spotify