OnlyFounders

In this episode, Matt and Anne tackle the murky world of social media vanity metrics, debating whether a high follower count is a valuable business asset or just a digital mirage. Anne shares her temptation to artificially inflate her audience to serve as a resume for her speaking career, while Matt strongly cautions against the ethical and algorithmic consequences of buying bot followers. They al...

Matt and Anne kick off this episode debating the merits of the "mental health day" versus the classic grit of powering through an illness. Anne shares her philosophy on working intuitively and trusting your energy to get tasks done faster , while Matt questions how that fluidity applies to the rigid demands of a startup. The conversation then takes a sharp turn into the realities of lead...

In this episode, Anne and Matt sit down with color specialist, artist, and former DIY Network TV host Shannon Kaye to explore her unconventional and highly creative career path. From starting as a decorative painter focused on making others' work shine to being unexpectedly thrust into the spotlight as a reality TV host, Shannon unpacks the hidden complexities of the design and television ind...

In this episode, Matt and Anne welcome guest Ben Whitehair , a unique "actor-preneur" who has mastered the art of building businesses alongside a career in Hollywood. Ben shares the journey of his college-founded startup that saved students $30 million and discusses how his current role at the feminist nonprofit Calling All Crows utilizes the same "CEO mindset" required for cre...

Everyone thinks wedding planning is just pretty flowers and cake tasting. In this episode, industry veteran Carly Rae (founder of Carly Rae Weddings & High Noon Floral) joins Anne and Matt to reveal the gritty reality of managing high-stakes events, from "burning" medical records to burning the midnight oil for Hollywood celebrities. Carly breaks down her journey from undercutting th...

The duo explores the critical shift from billing for time to billing for impact, with Anne explaining how she now ruthlessly deletes tasks that don't directly serve her top three yearly goals. Matt argues that the job market is evolving into a landscape of "mini venture capitalists," where employees are hired not for a specific role, but to own an outcome entirely using AI tools. Th...

Matt and Anne explore the argument that politics is often just a "metagame" that distracts founders from the hard work of building a business. They discuss the dangers of rigidity—suggesting that if you are inflexible in your political beliefs, you are likely inflexible in your business strategy as well. Anne shares her perspective on overcoming a "people-pleaser" mentality to...

Matt and Anne discuss the delicate balance of founder energy and the obligation to "show up" for clients, even when Friday feels like a Sunday. The conversation moves to Anne's strategic pivot with Fix & Form, targeting high-stakes M&A and healthcare companies rather than solopreneurs. Matt identifies a dangerous gap in her focus: prioritizing operations and fundraising over...

In this episode, Matt breaks down the discipline required to manage technical debt, explaining why ChipBot rejects nearly 90% of feature requests to prevent the product from becoming bloated. The conversation shifts to the rapid evolution of AI video, where Matt highlights how open-source models are beginning to challenge restricted platforms like Sora. Finally, Anne and Matt discuss the strategy...

In this episode, Anne and Matt discuss the fallout from X’s Grok and the disturbing rise of AI-generated exploitation. They argue that while the tools themselves—like Photoshop before them—are just instruments, the true burden of safety lies with the social media giants who control distribution. The discussion covers the futility of federal regulation in the US, the potential for state-based solut...

In this episode, Matt and Anne explore how to kickstart momentum when the team is lagging behind the founder's energy. While Anne emphasizes the importance of social connection and viewing the team as a "second family" to build identity and engagement , Matt pushes back, arguing that viewing business as family is a mask that hides the reality of business mechanics. The two compare t...

Matt and Anne return from the holiday break battling "January brain fog" and a wave of post-vacation sickness to tackle the myth of the "10X Revenue" goal. They discuss why setting revenue targets is often a recipe for failure because revenue is a lagging indicator you cannot control. Instead, they argue for 10Xing the "unsexy" inputs—activity, outreach, and product q...

In this episode, Anne reveals how saying "no" to traditional holiday travel unlocked her most productive week of the year. While Matt joins from the road in Chicago, the two discuss the power of "breaking the cycle" of family obligations and the necessity of advocating for your own schedule—introducing the non-negotiable concept of "Anne's Time". From drafting a...

In this episode, Matt and Anne dive deep into the often misunderstood dynamic of setting boundaries. While Anne advocates for boundaries as a critical tool for self-worth and ensuring others feel seen, Matt challenges the traditional view with a goal-oriented approach where unwavering directness is often just efficiency in disguise. From Matt’s six-week table tennis training blocks to Anne’s decis...

In this episode, Matt joins from the US Open in Las Vegas to break down how a loss in table tennis revealed a critical lesson in business strategy: the importance of sticking to your plan even when the opponent adapts. The conversation then pivots to the volatile landscape of Artificial Intelligence, where Matt argues that OpenAI is facing a "survival issue" as Google’s Gemini and open-s...

Matt and Anne unpack one of the hardest mental shifts founders face: moving from trading time for money to building something outcome-driven . What starts as a casual conversation about coffee and creatine quickly turns into a deep dive on pricing ethics, discount traps, burnout, pivoting (aka quitting), and why so many service businesses struggle to ever become real products. They explore why con...

Matt and Anne dig into what it really looks like to step into a new identity before you feel ready. Anne shares a major personal and business shift—repositioning Fix & Form as a Denver branding firm , committing to local growth, and finally claiming “speaker” as part of her professional identity. The conversation goes deep on integrity versus shortcuts, why faking momentum rarely matters, and...

Matt Lo and Anne Gillaspie unpack a deceptively simple idea with massive implications for founders: your environment dictates your mindset — and your mindset dictates outcomes. This episode starts with content creation vulnerability and ends somewhere much deeper: how founders survive chaos, context switch without burnout, and build momentum when everything they do pulls them in different directio...

Some episodes wander into gold on accident—this is one of them. On a snowy Denver morning, Matt and Anne fall into a raw, surprising conversation about early-career scrappiness, ego in your 20s, asking “dumb” questions as a superpower, and why distilling chaos into a single clear droplet is the mark of a strong founder. They unpack how emotional maturity shapes work dynamics, why some leaders stop...

December feels like a graveyard month for most founders, but in this episode Matt and Anne unpack why that mindset can quietly sabotage momentum — and how different business models create different “earned” slow seasons. They dive into founder psychology, burnout avoidance, backlog guilt, why product companies and service companies have opposite Q4 realities, and how to think about “impact windows...

When founders say, “We’re ready to grow — now what?” they’re usually staring at a cold engine with no momentum. In this episode, Matt and Anne unpack why early-stage marketing feels impossible, why 90–95% of ideas fail, and why A/B testing is useless before you have volume. They dig into the real levers a small business can control: consistent output, memorable creative, and accepting that momentu...

We sit down with marketing strategist and podcast host Kristi Mitchell , whose journey from corporate burnout to seven years of thriving entrepreneurship is anything but ordinary. Kristi opens up about her rocky exit from corporate life, the unexpected push from her husband that reignited her business, and the uncomfortable-but-transformative leap into full-time ownership. We get into the messy re...

Matt and Anne dive into the strange tension between being wildly busy yet weirdly unfazed by it. Matt’s been running on four to six hours of sleep while juggling new ChipBot features, US Open training, and a schedule only a “partial nomad worker” could maintain — yet insists he’s not brain-dead, just operating in “GPT-5 Thinking Mode.” Anne challenges him on how he stays functional, which leads th...

Matt and Anne sit down for a wide-open conversation about one of the biggest questions hovering over today’s tech world: Are we living in an AI bubble? They break down the trillion-dollar AI contracts, why enterprise AI pilots are failing at staggering rates, and how data pipelines—not the models—are the real bottleneck. From trust, regulation, and bias inside the weights… to AI as a household too...

Matt and Anne strip away the motivational-poster clichés and unpack the uncomfortable reality behind the phrase founders love to use but rarely define honestly. Anne opens up about the tension between ambition and parenthood, the limits of her available time, and how she’s restructuring her days to protect her flow state. Matt breaks down why “all in” is less about hours and more about output — an...