Too Direct with Stella Garber

Too Direct with Stella Garber

Stella Garber has been told her whole life that she is too direct. Too bossy. Too aggressive. She heard it as a kid. She heard it as a young manager. She’s heard it her entire career. And she’s spent years wondering whether she’d be getting that feedback at all if she were a man. Her answer: absolutely not. Stella is a repeat founder and the co-founder and CEO of Hoop, an AI customer support agent for e-commerce brands. She’s also Eastern European, a self-described high D on the DISC profile, and someone who has figured out - through years of managing remote teams, navigating co-founder relationships, and doing a lot of internal work - how to stop softening herself and start channeling her directness more effectively instead. In this episode, she talks about what it actually took to get there: the DISC framework she runs with every team she builds, the Claude project where she stores her co-founders’ profiles to prep for hard conversations, and why she thinks the real work of building a company - the seven-to-ten-year stretch after launch that nobody talks about - depends entirely on who you choose to do it with. What you’ll learn: * Why “don’t be so direct” feedback - however well-intentioned - is often gendered, and what Stella thinks would happen if a man got the same note * The one context where Stella thinks directness actually did need calibrating, and how she learned to root it in relationship first * How she uses DISC profiles across her founding team, and why she keeps them loaded in a Claude project for sensitive conversations * What it sounds like when a high-D founder talks to a C co-founder: fewer claims, more metrics, and a much better outcome * Why self-awareness is a double-edged sword for founders, and what you gain and lose at each stage of the journey * The values exercise Stella and her co-founders did before they had a product, a raise, or even a company name, and why she thinks it’s the single biggest thing that makes co-founder relationships last * Why who you partner with is the most important determinant of your long-term success as a founder * What the real timeline of company building actually looks like, and why the emphasis on launching gets it completely backwards About Stella Garber Stella Garber is a repeat founder and the co-founder and CEO of Hoop, an AI customer support agent built for e-commerce brands. She has spent essentially her entire career working remotely, and has built and led distributed teams long before it became standard practice. Stella has co-founded with the same partners twice, first working alongside them, then building with them, and is a strong believer that the foundation of any company is the values conversation you have before you write a single line of code. She is a high-D DISC profile, an Eastern European who has heard “too direct” more times than she can count, and a founder who has turned that feedback into a leadership philosophy: know yourself deeply, build in the counterbalance, and find the people who bring out your best. This episode is for anyone who has been told to soften their edges, and is starting to wonder if the problem isn’t them, it’s the framing. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Stella on LinkedIn [https://www.linkedin.com/in/stellagarber/] 🤖 Learn more about Hoop: hoop.app [https://hoop.app]

If Not Me, Then Who? with Joy Hoover

Joy Hoover invented a lipstick with a panic button in the base and a drink-testing strip in the cap. She built a national nonprofit from nothing over 12 years that landed in the top 10% in the country. She won Top Tech of the Year in 2024. And when she decided to run for Congress - going up against a 14-year incumbent in a district that hasn’t flipped since 1972 - the people around her told her it would hurt her business, blacklist her, and blow up everything she’d built. She considered the advice for months. She looked at smaller seats. She tried to talk herself out of it. And then she couldn’t get it out of her gut. Joy is the founder and CEO of Esōes Cosmetics (SOS), a safety tech company built to fight the epidemic of sexual and domestic violence - a cause she’s been working on for 16 years in her community. In this episode, she talks about what it takes to keep going when the establishment tells you to stay in your lane, why she thinks more founders should run for office, and why she answers yes every morning even when she doesn’t feel like it in the afternoon. What you’ll learn: * Why “it will hurt your business” advice - from the political establishment - almost stopped Joy from doing the thing she was most built to do * What Joy invented, why she invented it, and the investor question that shocked her: “Why does anyone need that lipstick?” * The mix of passion and delusion that Joy says every founder needs, and why she’s leaning on it now more than ever * Why she couldn’t get Congress out of her gut, even when the timing was terrible and she was still displaced from a house fire * What running a congressional campaign has in common with building a company from scratch * Why she called every one of her 100 angel investors before announcing her run, and the reaction she’ll never forget * Why Joy believes more founders should run for office, and what the 17% statistic says about who’s wired for it * Her advice for anyone whose gut is pulling them somewhere people are telling them not to go: know your why, find your people, and ask yourself every morning if it’s still worth it About Joy Hoover Joy Hoover is the inventor, founder, and CEO of Esōes Cosmetics (SOS), a safety tech company that makes a first-of-its-kind tech-enabled lipstick, with a panic button that can dispatch authorities and a built-in drink-test strip for detecting drugging. Before SOS, Joy spent 12 years building a national nonprofit focused on anti-trafficking and anti-violence work, growing it to the top 10% in the country. She has zero background in engineering or science. She won Top Tech of the Year in 2024 anyway. She is currently running for US Congress in Nevada’s First District, challenging a 14-year incumbent in a race that hasn’t been won by a challenger since 1972. She launched her campaign while displaced from her home after a house fire. She has 100 angel investors, a husband who came around, and a gut she’s learned to trust. This episode is for anyone whose next step looks too big, too risky, or too unlikely, and who is trying to figure out whether that’s a reason to stop or a reason to go. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Joy on LinkedIn [https://www.linkedin.com/in/joyehoover/] 💄 Learn more about Esōes Cosmetics: esoescosmetics.com [https://esoescosmetics.com]

Scotty’s Little Sales Club Will Never Work with Scott Leese

Scott Leese’s first sales manager pulled him into his office, looked him dead in the eye, and told him to stop caring so much about his people. Stop going to lunch with them. Stop being their friend. Draw a harder line. Then he said something that has lived rent-free in Scott’s head for over 20 years: “Scotty’s little sales club is never gonna work.” Scott didn’t listen. He built his teams the way he wanted to; caring about the person first, more than the number, more than the company, more than the founders’ eventual payday. He hired the people everyone else passed on: someone living in their car, someone just out of prison, single parents rebuilding from scratch. He never looked at a resume. He asked people where they wanted to go and why they were finally ready to do what they’d been unwilling to do before. And he won. Over and over. He’s a six-time sales leader, serial entrepreneur, consultant to early-stage founders, and the guy who eventually named his own coaching community Scotty’s Little Sales Club… out of spite. In this episode, he talks about where that stubbornness comes from, what four years in the hospital taught him about what actually matters, and why caring about humans isn’t a soft strategy - it’s the only one that holds up. What you’ll learn: * Why “draw a harder line” advice - from people who confuse rigidity with leadership - can cost you the trust that actually drives performance * What Scott’s four years in the hospital (and the years rebuilding after) gave him that no business school ever could * How he built his teams by betting on the people everyone else had already written off. and why it kept working * What his one-on-ones actually looked like (hint: no pipeline reviews, lots of walks around the building) * Why telling your employees that AI is going to replace them is not just tone-deaf - it’s strategically dangerous * What the VC ecosystem looks like right now and why founders may need capital less than they think * The one question he asked every candidate instead of reading their resume: why are you willing now to do what you’ve previously been unwilling to do? * Why “treat humans like humans” is the through-line from early sales leader to serial entrepreneur to founder coach About Scott Leese Scott Leese is a six-time sales leader, serial entrepreneur, and the founder of Scott Leese Consulting, where he works with early-stage companies navigating the zero-to-$25M go-to-market journey. He also runs Surf and Sales Summit, a consumer product business, a landscaping company, two venture capital firms, and two podcasts - because apparently he can’t stop starting things. Scott came to his career late: after four years in the hospital, nine surgeries, and kicking an opioid dependency at 27, he walked into his first sales job with no resume worth looking at and the unshakeable conviction that whoever took a chance on him wasn’t going to regret it. They didn’t. He’s spent the 20 years since paying that forward — hiring the people others overlook, leading teams with radical openness, and building a reputation as someone who genuinely gives a shit about the people who work with him. This episode is for anyone who has been told their style is too soft, their team is too close, or their people skills are getting in the way of real leadership - and is wondering whether the person saying that has ever actually built anything worth following. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Scott on LinkedIn [https://www.linkedin.com/in/scottleese/] 💼 Learn more about Scott Leese Consulting: scottleeseconsulting.com [https://scottleeseconsulting.com/]

Show the Real Chapters with Brooke Sellas

During COVID, Brooke Sellas posted something honest on Instagram - two words: “I am so tired.” She wasn’t complaining. She was being human. The mentor she’d hired to help her build her personal brand told her it was a mistake. Leaders only show the good parts, they said. Brooke almost believed it. Brooke is the founder and CEO of B Squared Media, a social media agency she bootstrapped - with no funding, no sales team, just herself - to a seven-figure business over 14 years. Her company’s whole philosophy is built on a trademarked tagline: Think Conversation, Not Campaign. So when a paid expert told her to hide her real feelings and only project perfection, it didn’t just sting personally. It cut against everything she’d built. In this episode, she unpacks why that advice was so damaging, why she almost took it anyway, and what it actually takes to trust yourself when someone you respect tells you you’re wrong. What you’ll learn: * Why “only show your best self” advice - however well-intentioned - can quietly undermine the trust you’re trying to build * The social penetration theory Brooke studied in college that still explains why vulnerability works on social media (and in business) * What she did when a mentor lambasted her for showing up authentically, and how long it really took to recover * Why imposter syndrome hits women founders harder, and what helped Brooke finally snap out of the spiral * How to build discernment about whose advice is worth taking, and how to spot when advice isn’t actually coming from a good place * The question every founder should ask before taking advice: “Who benefits from me doing this?” * Why Brooke now publicly shares when her business is down, and what happened when she did About Brooke Sellas Brooke Sellas is the founder and CEO of B Squared Media, a social media agency specializing in VIP customer care on social channels for enterprise clients. She bootstrapped B Squared to seven figures over 14 years without outside funding or a sales team. Her company’s approach is rooted in a simple but powerful idea - Think Conversation, Not Campaign - and in the psychology of how humans actually build relationships and trust. Before founding B Squared, Brooke spent years in social media strategy at another company, and her undergraduate thesis on the social penetration theory has shaped her philosophy ever since. She’s a connector, a community builder, and a founder who has learned - sometimes the hard way - that being real is always the right strategy. This episode is for anyone who has been told to put a better face on it, and is wondering whether their real face might actually be the better strategy. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Brooke on LinkedIn [https://www.linkedin.com/in/brookebsellas/] 💼 Learn more about B Squared Media: bsquared.media [https://bsquared.media]

Be More Difficult with Katie Robbert

Katie Robbert has been told to stay quiet, stay in her lane, and let someone else be the face of the company. She heard it from a mentor she respected. She heard it from investors. She heard it so many times she almost believed it. She didn’t.  Katie is the CEO of Trust Insights, an AI education and analytics firm she co-founded eight years ago. And she holds that title deliberately, because someone told her she shouldn’t.  In this episode, she pulls back the curtain on what it actually took to get there: the verbally abusive VP she was told to just tolerate, the investor feedback that nearly made her hand over the CEO seat, and why she’s now built a virtual version of herself to run ideas past before they get to her. The answer is always the same: it’s going to ask a million questions. What you’ll learn: * Why “don’t rock the boat” advice - however well-intentioned - can quietly wire you to shrink instead of lead * What Katie did when investors told her a female CEO would tank her chances of funding * How to tell the difference between a battle worth fighting and one that will just cost you * Why the people who say yes to everything are the ones who keep leaving, and what Katie looks for instead * How Trust Insights built a virtual Katie Robbert AI trained on her own decision-making style (and why the team runs ideas past it first) * What real community looks like for founders who need someone to be honest with - not impressed by them About Katie Robbert Katie Robbert is the CEO of Trust Insights, a data analytics and AI education firm she co-founded with Christopher Penn in 2017. With over 15 years in AI and analytics, she has built a reputation for asking the questions other people are afraid to ask - in client work, in company culture, and in every room she walks into. Trust Insights serves organizations navigating real-world AI adoption and has been a resource in the space long before generative AI became a boardroom talking point. Katie is an introvert who runs a public-facing company, a pragmatist who works alongside one of the most innovative minds in marketing AI, and a CEO who was told she shouldn’t be one. This episode is for anyone who has been handed advice that was really just a request to make themselves smaller — and is trying to figure out when to ignore it. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Katie on LinkedIn [https://www.linkedin.com/in/katierobbert/] 💼 Learn more about Trust Insights: https://www.trustinsights.aitrustinsights.ai [http://trustinsights.ai]