Startup Therapy

Ever gotten startup advice that sounded like a fact—but was really just someone’s confident opinion? This episode breaks down why so much startup advice is dangerous, especially from well-meaning advisors who lack self-awareness about their bias and the weight their words carry. Ryan and Will unpack how founders, who often can’t tell “ground truth” from bravado, can be pushed into bad decisions by overconfident feedback—particularly from investors and local “yokels” with narrow worldviews. They share examples from pitch competitions and boardrooms, argue that delivery is often more harmful than the advice itself, and highlight “you might consider” as...

Ever wonder which “version of you” should show up to dinner, a board meeting, or a team update? This episode breaks down why founders feel like they’re constantly auditioning different personas—optimistic forecaster, calm leader, guarded partner—because the honest answer (“I don’t know” or “we’re struggling”) can carry real consequences with investors, employees, customers, friends, and family. The conversation explores the difference between confidence about an uncertain future versus crossing into deception, the emotional burn rate founders pay to stay composed, and how compartmentalization becomes muscle memory—even through illness, grief, or shutdowns. They highlight how group dynamics push...

What if you could build a working prototype without giving away half your company? The episode argues that tools like Claude have ended the old “technical co-founder as early-stage gatekeeper” dynamic: founders used to need a developer to cross the first binary hurdle from idea to product, and some investors also pushed for technical co-founders before funding. Now, founders can ship prototypes in a weekend with an AI subscription, pushing the vulnerability window later and repricing equity. The hosts stress technical talent still matters—especially for scaling and real engineering—but AI exposes the difference between people who only had scar...

What are you actually willing to do to get what you want as a founder? Using Will’s 6:00 a.m., 15-degree framing session and a dumpster-diving Bobcat mishap as metaphors, this episode breaks down what separates founders from everyone else: an “unreasonable” willingness to do hard, risky, uncomfortable things repeatedly—often without any guarantee of payoff. The conversation explores the real price founders pay (uncertainty, rejection, sacrifice, and daily grind), why high achievers used to clear reward loops can struggle in startup chaos, and why outsized outcomes tend to follow people who endure what others won’t. They also unpack com...

What happens when AI turns your hard-won moat into a weekend project? This episode argues that AI has effectively forced established companies back into “startup mode,” wiping out long-held assumptions about products, staffing, and competitive advantage. Will and Ryan break the reset into three shifts: the cost to build and operate has collapsed, big teams and legacy systems have become liabilities, and “everything is buildable” faster than incumbents can adapt. They warn that competitors can now reach product parity quickly and survive with tiny teams that don’t have payroll to protect, making old “wait them out” strategies obsolete. The hardest pa...

Ever notice how people show up loudest after you’ve already won? This episode digs into why founders often get the least support when the risk is highest—and the most opinions once success is “de-risked.” Will shares early moments of having virtually no safety net (including starting with $19, dropping out, and getting doubted), contrasted with the few timely “bricks” that actually changed his trajectory—like a risky $10K loan and a friend’s family offering a place to stay for the holidays. They unpack how funding wins, press, and exits attract late-arriving fans, opportunists, and advice that can derail post-succ...

What if building a company is the fastest way to find out what you’re actually capable of? This episode explores how startups don’t just get built by founders—startups build founders by forcing them into new roles like finance, sales, marketing, design, legal, and leadership, often before they feel ready. Will shares how real stakes (like cash flow and payroll) turned “I’m bad at math” into practical financial skill, and why getting to ~80% proficiency across key areas creates leverage, better decision-making, and protection against getting bullshitted. The conversation digs into how exposure and environment unlock hidden potential (f...

What if “retirement” for founders isn’t about stopping work, but finally getting relief? The conversation unpacks why builders rarely stop building: founders are wired to create, not to consume, and the fantasy of beach life usually shows up at a low-energy point when what’s really needed is recovery. They compare founder burnout to wanting the finish line without running the race, and note how exits often lead from “margaritas” to “domain names” within months because the calling returns once the nervous system resets. The key reframe: separate a recovery plan from a retirement plan, and define “retirement” as creating on your...

Ever feel like you’re “almost ready” to launch—just one more feature, plan, or credential away? This episode argues that “ready” isn’t a prerequisite for startups; it’s the result of starting and getting real market feedback. Using examples like selling early software for $1,500, learning web building on the fly, a disastrous (but educational) client pitch moment, and even an impulsive scuba dive, the discussion shows why planning can become productive-looking theater when nothing is being tested. The real cost of waiting isn’t just lost time—it’s lost learning, missed customers, and negative compounding versus competitors who take a...

Why do founders fight over giving an investor 15% but hand out huge chunks to co-founders, employees, and advisors with far less certainty of return? The episode argues that investor dilution is often the cleanest trade because cash and terms are clear, while “everyone else pays in maybes and promises.” It warns that early-stage equity feels worthless but represents 100% of a company’s future value, so giving away 50% to a near-stranger can become a permanent cap table problem that also costs speed, optionality, and sanity. Practical fixes include vesting, cliffs, tying equity to real value creation, defining what happens if someon...

Ever wake up at 3:00 AM convinced your startup is about to break? The conversation unpacks how founders can’t really “leave work,” and how constant vigilance can turn into fear dressed up as responsibility—endless rumination that produces stress, not decisions. Will shares decades of 3:00 AM worry cycles, the superstition that anxiety prevents disaster, and how even vacations get hijacked by disaster simulations (including getting hacked on the way to Comic-Con). They draw a line between real thinking that creates options and looping that creates suffering, then discuss practical replacements: box breathing to fall back asleep, gratitude to reset perspect...

What happens if building a startup no longer requires a team? The conversation explores how AI is rapidly turning the classic “product + developer + marketer” founding trio into an optional choice, making one-person companies the new default as tools get dramatically better and far cheaper than hiring. They unpack how this shift changes equity, speed, and the quality filter that co-founders and teams used to provide, while also threatening many “on-ramp” roles like customer support and other knowledge-based services (accounting, payroll, legal). They wrestle with the economics that push founders toward AI, the competitive pressure that makes it feel unavoidable, and the...

What are you really trying to fix by building this company—and what happens when you finally admit it? The conversation unpacks how founders often default to a public “change the world” story while their private motive is something more personal like safety, control, validation, belonging, autonomy, or even revenge. When that real why stays hidden, decisions get miscalibrated and founders chase the hardest possible path (like massive VC rounds) even when a smaller outcome might satisfy the true need. They discuss how these motives “leak out,” especially after selling a company and realizing you’re no longer needed, and why succ...

Worried about “losing control” because of dilution? This episode breaks down why equity is a poor proxy for control in startups: the cap table splits money, while control is defined by decision rights in the operating agreement and enforced through board voting. The hosts explain how founders can own most of the company yet still need permission for key actions (like senior hires), how boards are built (often 2 founders, 2 investors, 1 independent), and how board math can outweigh founder ownership—especially when things go wrong. They also cover how operating agreements get rewritten each funding round, how founders can be fired...

Ever feel like you hit a milestone in your startup and immediately get handed the next problem? The episode explores why startup work rarely delivers a true sense of “done,” how founders get trapped by the arrival fallacy (believing the next round, milestone, or cushion will finally bring relief), and how the constant threat of being “eaten” by faster competitors turns ambition into paranoia. Ryan and Will compare the endless nature of startups to more finite work, discuss how chasing metrics and despising complacency fuels chronic restlessness, and share personal examples of goals that didn’t bring fulfillment. Their takeaway...

Ever feel like you’re working nonstop and still falling behind? The discussion argues founder happiness and decision-making improve fastest by recalibrating expectations, because “happiness = reality ÷ expectations.” Using stories from trading work for pizza or restaurant tabs to later winning massive business, it highlights how low expectations can make progress feel rewarding, while the “snowflake myth” and unpriced optimism create entitlement and disappointment. They distinguish aspiration (what you’d like) from expectation (what must happen), urging founders to replace unicorn fantasies with concrete, earned milestones like revenue, payroll, and product-market fit. They stress startups take far longer than most timelines cla...

What do you think really happens if you burn out and step away for a minute? The conversation breaks down how founders often imagine an apocalyptic chain reaction—customers leaving, the team collapsing, investors panicking—when in reality burnout is a predictable capacity ceiling and most worst-case scenarios don’t happen. They argue the real danger is pretending burnout won’t come, pushing until physical failure, and keeping recovery secret, which can create the chaos founders fear. Using sports analogies, they emphasize that staying “on the field” nonstop makes you a liability, and that planned breaks build resilience, give teams room t...

What if the thing that looks like a distraction is actually the move that saves your startup? This episode breaks down why the “stay focused at all costs” advice can be risky when you’re still figuring out what actually works. The hosts challenge the myth of the linear startup path, arguing that side quests—small, intentional experiments with capped downside—create learning, reduce single points of failure, and help you earn the right to pivot with evidence instead of vibes.

They share how Fundable’s early equity crowdfunding push revealed founders were unprepared to raise money, which led to...

What if failure isn’t something to avoid, but a skill to master? This episode breaks down why startups can’t be built on certainty—new markets, new products, and new teams mean you’re guaranteed to be wrong a lot. The goal isn’t to “be right,” it’s rapid error correction: make decisions, ship anyway, learn fast, and recover even faster. The conversation covers how avoiding failure leads to paralysis (“steering a parked car”), why indecision compounds in startups, and how to reduce risk by keeping failures small, reversible, and frequent (kill switches, stop rules, and capped losses). They share...

Is AI truly the game-changer for startups, or does it bring unexpected chaos? This episode dives into how AI is transforming forecasting, marketing, product development, employment, and investment in the startup ecosystem. Ryan Rutan and Will Schroter discuss the rapid pace of change brought by AI, including the exciting opportunities and the unsettling uncertainties. They explore how traditional pillars of business like hiring, marketing, and customer acquisition are being upended, creating both new challenges and avenues for innovative founders to thrive. Tune in to understand how to navigate this AI-driven landscape and leverage the chaos for maximum impact.

How has the relentless pursuit of efficiency, aided by tools like remote work, Zoom, Slack, and AI, affected our human connections? In this episode, we're exploring the cost of optimized workflows on our humanity. We delve into personal anecdotes and discuss the ramifications of isolation in the workplace and the loss of shared experiences. We also contemplate the importance of reintroducing human interactions to ensure a balanced, connected, and more fulfilled work environment.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
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What will AI do to everything? In this episode, we explore how AI is set to create a surge in new startups, reshaping employment as we know it. As jobs get displaced, the concept of big employment shifts, giving rise to smaller, more agile companies using AI tools. Drawing parallels with past technological revolutions, we highlight the opportunities that lower costs and new market demands present for founders. We discuss the transformation in various sectors, from customer service to content creation, and emphasize how AI can democratize entrepreneurship globally. Finally, we delve into the exciting potential for startup growth...

Ever felt like vacations just aren't cutting it when it comes to startup burnout? In this episode, Ryan Rutan and Will Schroter dive deep into why burnout is inevitable for founders and how quick fixes like vacations often fail to address the root of the issue. They explore how to truly recover and maintain that all-important spark in your work. Learn why it's crucial to inventory what drains and fuels your energy, and how making meaningful changes—not just taking time off—can lead to sustainable recovery. Real-life examples and practical advice make this a must-listen for any founder feel...

Can founders turn delusion into success? In this episode, Ryan and Will discuss the essential role of optimism in startups. Drawing parallels between founders and firefighters, the duo explores how belief against all odds drives entrepreneurs forward. They explain how maintaining optimism is not just about having a positive outlook but about creating momentum from minor wins and leveraging chaos as an opportunity. The hosts also address the fine line between optimism and dishonesty, emphasizing the importance of an 'educated wish.' Whether you're battling to raise funds or struggling to maintain morale, this episode delves into why a...

Ever find yourself caught in the trap of confusing visibility with progress? In this episode, we'll delve into why seeking attention can often feel like momentum but doesn't necessarily translate to business traction. Will Schroter shares a cautionary tale from his own experience, revealing how his focus on brand-building and networking kept him from truly building his company. We explore the fine line between personal branding and productivity, and why many founders need to prioritize the latter to achieve real success. It's a reminder that until your product and business are fully developed, every external interaction could be costing...

Is getting bigger always better for startups? This episode dives into the hidden costs of scaling up and how growth can sometimes make a company worse, not better. Ryan and Will discuss the trade-offs between size and quality, using examples like Google and PayPal. They explore how rapid growth can diminish company culture, slow down decision-making, and introduce inefficiencies. The conversation also covers personal experiences in startup growth, emphasizing the importance of optimizing for better rather than just bigger. Whether it's adding more staff or raising capital, they advocate for making decisions that enhance company quality and founder life...

Ever wonder if being your authentic self at work might sometimes do more harm than good? The delicate balance of authenticity and diplomacy in leadership. From discussing the rare contexts where pure honesty works, to sharing personal anecdotes about navigating the consequences of unfiltered truth, this episode unpacks how transparency can impact your team, brand, and personal relationships. Find out why being your true self might only be great advice 6% of the time and how effective communication can save you from unintended fallout.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website<...

Are you convinced that you need to fix all your flaws as a founder? In this episode, we explore why that's not necessarily true. Ryan and Will dive deep into the idea that both startups and their founders are loaded with problems, some of which aren't really 'problems' at all but hidden superpowers. From obsessive tendencies to ADHD, they discuss how to harness these traits for success rather than trying to fix them. Drawing from personal experiences and industry insights, they touch on the influence of pharmaceutical marketing, the role of social media in shaping perceptions, and the importance...

Have you ever wondered if remote work is better than being in the office? Ryan and Will dive into their experiences and how their work culture has evolved over 20 years. They discuss the pros and cons of remote work, the importance of autonomy, and how remote setups have stripped away some of the overhead, revealing who truly thrives in this environment. They also explore whether it's possible to create a strong company culture remotely and how the shift has amplified the best and worst in employees. Tune in as they break down their journey from being die-hard office goers...

Ever dreamt of handing off your startup to a killer operator and sipping margaritas while the money keeps rolling in? It sounds perfect, but reality often has other plans. In this episode, we break down why passing on the reins isn't as smooth as it seems—from the slow degradation of everyday tasks to the irreplaceable instinct and urgency a founder brings. Discover why certain roles and tasks can be handed off successfully while others, like maintaining culture and strategic vision, often falter without the founder's unique touch. Tune in for practical advice on what you can actually hand of...

Ever wonder what happens when a founder gets 'promoted' out of the CEO role? Ryan and Will dive into the tricky terrain of founder transitions, exploring how it feels to be nudged into roles like Chief Vision Officer or Chairman—positions that often come when a new CEO is brought in. They discuss the emotions involved, the motivations of investors, and the strategies for turning this awkward moment into an opportunity. Whether you're in the thick of this situation or just want to be prepared, this episode provides valuable insights on maintaining dignity, negotiating effectively, and leveraging a graceful ex...

Ever felt like burnout is inevitable in your startup journey? You're not alone. Burnout can feel like a silent co-founder, but it doesn't have to signal the end of your entrepreneurial story. In this episode, we discuss why burnout happens, how to diagnose it, and most importantly, how to treat it. Discover the importance of pacing yourself, the hidden costs of burnout, and why taking a break is crucial—not just for you, but for your entire team. We'll share personal anecdotes, practical tips, and the value of stepping away to recharge, so you can return stronger and more pa...

Ever feel like you need more hours in the day? Turns out, you don't. In this episode, we dive deep into time management for founders, starting with a viral Reddit post that stirred some controversy. We'll explore how compressing your timelines can lead to greater efficiency and free up your schedule for the things that truly matter. Forget the chronic meeting bloat and endless email chains; it's all about optimizing every minute. Discover how focusing on small, incremental tasks can lead to significant progress, both in your professional and personal life. Whether you're a solo founder or leading a...

The complexities of alignment among founders, employees, and even spouses. They debunk the notion that perfect alignment exists, emphasizing that often, perceived alignment is more fiction than reality. The conversation covers the inevitable differences in expectations, contributions, and risk tolerances that arise between co-founders and employees. The hosts also delve into the personal side, exploring how founders' professional decisions impact their relationships at home. Through candid anecdotes and practical insights, they highlight the importance of mutual respect and understanding in managing these fundamentally misaligned expectations in both business and personal life.

Resources:
Startup Therapy Podcast
...

The challenging question of whether the sacrifices made in pursuit of entrepreneurial success are ultimately worth the payoff. Will retells his personal story of almost buying an expensive house in Bel Air only to realize, thanks to his wife's intervention, that it wasn't what he truly wanted. The duo explores themes of sacrifice, payoff, and how aligning personal goals with true desires can lead to genuine happiness and fulfillment. Whether it's the freedom to travel or the joy of creating something with your hands, this episode urges founders to carefully contemplate their end goals and ensure their sacrifices lead...

The critical do's and don’ts after a big financial win as a startup founder. They emphasize the importance of not oversharing about your wealth, shifting from an offensive to a defensive mindset, preserving your gains, and being cautious about new investments. They also explore how to handle the psychological and social challenges that come with newfound success, using real-life examples and practical advice to ensure you don't blow your hard-earned money.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.li...

Ryan and will talks about a critical issue many founders face: knowing when to say 'enough is enough.' They explore the constant pursuit of growth both personally and professionally and how it can turn into a liability if not checked. They dive into the psychological roots of why founders struggle with the concept of 'having enough,' the impact of a scarcity mindset, and the importance of recognizing diminishing returns. The hosts share personal anecdotes and offer practical advice on how to balance ambition with fulfillment, emphasizing the need for diversified 'buckets' of happiness beyond just business success.<...

How entrepreneurship can transform lives and communities? Will shares his personal journey from a challenging childhood to becoming a successful entrepreneur. They explore whether entrepreneurship can be a means to alleviate poverty, emphasizing the importance of hope, a safety net, and access to education and mentorship. The conversation dives deep into the potential impact of entrepreneurial initiatives on economic development and the need for structured support to foster entrepreneurial success on a global scale.

Resources:
Startup Therapy Podcast 
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn 
ht...

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges and dynamics of blending friendship and professionalism in startups. They delve into the potential pitfalls of treating your startup team like a family, the consequences on both founders and employees, and the importance of setting clear boundaries. They highlight shared experiences from their early careers and emphasize the need for empathy, respect, and a professional approach to lead effectively without compromising authority.

Resources:
Startup Therapy Podcast 
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
L...

Ryan and Will talk about the growing role of AI in startups. They explore how AI is automating traditional founder tasks like writing, coding, and analyzing data. The conversation delves into the existential threat AI poses to the founder's role and how founders can adapt to this new landscape. They argue that founders should embrace AI to focus on creativity, curation, and leadership rather than being bogged down by routine tasks. The episode underscores the importance of evolving with technology to enhance productivity and innovation, ultimately redefining the founder's job description for the future.

Resources:
Startup...