Do Hard Things Podcast

"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."

“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.

"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.

"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."

"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."

"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.

"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."

"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.

"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."

"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."

"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."

"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.'"

"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."

"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."

"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.

"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."

"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."

"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."

"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."

"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."