TitleDalton + Michael
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2026
How Great Founders Approach SalesWhat does being great at sales look like in practice? In this episode of Dalton + Michael, the two dive deep into the topic of startup sales. It's a big topic, and there are lots of misconceptions out there, and so D+M talk through some of the common misconceptions as well as encouraging founders to see some sales advice they already know through fresh eyes.
Building A Big Company: Non-Obvious InsightsIn this episode of Dalton + Michael, the two discuss the risk a startup faces when: 1) it successfully made something people want but 2) the startup is at risk of hitting a "local maximum." To build a huge company a startup often needs to change direction/strategy post product-market fit. D+M discuss some examples of companies that executed on strategy changes post-PMF including Facebook and DoorDash.
Standard Capital UpdateIn this video, Michael interviews Dalton to get an update on Dalton's Series A fund, Standard Capital, since Standard's first ever application cycle was recently completed. They discuss what Dalton has learned so far, as well as some tips for founders that might be interested in applying to Standard in the future.
2025
2025 Year In Reviewn this end-of-year episode, Dalton and Michael discuss some of the biggest topics that came up for them in 2025 including: depopulation, San Francisco, AGI, self-driving cars, talk of AI bubbles, abundance and more.
Is My Startup Growing Fast Enough?Founders may have internalized the idea that if their startup isn't growing as fast as Cursor they are going to fail. In this episode, Dalton + Michael discuss if there is any truth behind this feeling, and discuss some of the fuzziness around growth metrics for AI startups.
Real vs Fake StartupsWhat is the difference between a "real" vs a "fake" startup? Dalton and Michael discuss the difference between founders doing the real work of building and talking to customers vs pretending, and offer guidance for how founders should think about role models. As Michael says, its never too late to fix!
How To Get Better AdviceAfter doing office hours with thousands of Y Combinator companies over the years, Dalton and Michael discuss some tips and tricks on how to make the most of an advice session with an investor or mentor.
Stop Obsessing Over Fundraising AnnouncementsHow does reading funding announcements make you feel? In this episode of Dalton + Michael discuss startup fundraising announcements and the strong reaction people have to them, particularly when it doesn't seem "fair."
Process vs Chaos In StartupsIn this episode of Dalton + Michael discuss their age old debate of how much process is too much vs too little. When you are designing a process are you creating art or manufacturing bolts?
How Impatient Should Founders Be In The Pre-AGI Era?In this episode of Dalton + Michael, the two discuss several topics: How impatient should founders be in the AI era? If it seems like everything is moving very fast, does that mean work that takes a while is not worth doing? Is there a cheat code to guarantee startup success?
Inside Standard Capital: New $425M Series A Fund, ExplainedIn this episode, Dalton + Michael discuss the background and details for Dalton's new Series A fund, Standard Capital. D+M discuss the key ideas and inspiration for Standard Capital from many years of working with founders at Y Combinator.
Dalton + Michael Return To YouTubeDalton Caldwell and Michael Seibel return to YouTube! In this episode the duo discusses big life changes and what led them to leave their jobs as Managing Partners at Y Combinator.
This Is What Young Founders Should Focus OnAt YC, we're seeing more and more people in their 20s taking the leap and starting their own companies. In this episode, Dalton & Michael share their advice on how young founders can get a head start and hit the ground running in their startup journey.
2024
How To Focus On The Right ProblemsWhen it comes to building a successful startup, focus is critical. But how do you know if you’re spending time on the right things? In this episode, Dalton and Michael share advice for how to break through the noise and zero in on solving the problems that matter most for your business.
How To Make The Most Out of Your 20sHow should you navigate your 20s - the most important decade in your life? For many people, it's an age with fewer responsibilities: no kids, no mortgage, no restrictions. And so it's actually the best possible time to go hardcore: to take risks, invest in yourself, and surround yourself with like-minded people. In this episode, Dalton & Michael share their thoughts on how to live your 20s - founder or not.
The AI Future Has Arrived: Here's What You Should Do About ItThanks to advances in AI, we're currently living through one of the biggest technological shifts in a generation. And things aren't slowing down anytime soon. So now the question is, what should you do about it? In this episode, Dalton and Michael break down several steps you can take right now to leverage the latest tools and set yourself up for success in the age of AI.
Meta VS Apple: What Their Battle Means For AI StartupsYou know what they say, to understand the future, look to the past. Since the early 2000s, Apple and Facebook (now Meta) have been battling over who controls the consumer market. Facebook arguably dominated the web era, while Apple took over during the mobile era starting in the late 2000s. Now, as we enter the AI era, Dalton + Michael discuss who's pulling ahead, and what that means for startups trying to break into the crowded consumer market.
What Founder Mode Really MeansThanks to a recent talk by Airbnb CEO Brian Chesky and a follow up essay by Paul Graham, the concept of "founder mode" is everywhere. But what does it mean and who does it really apply to? In this episode, Dalton and Michael break through the noise to find out what lessons can be learned from going all in on "founder mode."
The Times When Paranoia Fueled Technological AdvancementSpace travel, the Internet, cryptocurrency — these huge leaps in technology were fueled at least in some part by distrust and fear of others. In this episode, Dalton & Michael discuss the origins of some of the biggest innovations over the last 75 years.
Avoid These Tempting Startup IdeasThinking of a new startup idea? Dalton Caldwell and Michael Seibel discuss the types of ideas to stay away from — what we commonly refer to as "tarpit ideas."
Signs Your Company Is Recovering From ZIRPAs Dalton & Michael have discussed before, ZIRP stands for "Zero Interest Rate Policy" which refers to when the Federal Reserve sets interest rates around 0% and banks were able to borrow money for almost nothing. This phenomenon had a profound impact on tech throughout the pandemic and many companies are still readjusting. In this episode, Dalton & Michael examine how to know whether your company is recovering from a bad case of ZIRP (aka Zirpes) and how to know if it may be time to leave and do something else.
How To Live In The Social Media MatrixRemember how in "The Matrix," Neo found out that human beings were really just being used as batteries to power the machines that enslaved them? In a sense, social media companies are now the machines, and we, the users, have become the batteries. With that in mind, Dalton and Michael discuss what to be aware of as we engage online and how we can leverage the social media matrix to our benefit.
How To Influence Decision MakersWhether it's career advancement, leaving a positive mark at an org, or raising funds for your startup, the ability to convince and influence decision-makers is a vital skillset to develop. In this video, Dalton Caldwell and Michael Seibel discuss actions you can take to be more persuasive and create more favorable outcomes for yourself.
The Problem With Startup "Experts"Despite the most successful tech founders being centralized in the Bay Area, there are founders, accelerators, and investors located around the world. In this video, Dalton Caldwell and Michael Seibel discuss the phenomenon of local startup experts and why they may be doing a disservice to your entrepreneurial journey.
Tarpit Ideas: The SequelThe long awaited follow-up to their original tarpit ideas video, Dalton and Michael dispel some misconceptions about what a tarpit idea actually is and how it applies to current technology trends like artificial intelligence. Don't get stuck!
What Is ZIRP And How Did It Poison Startups?ZIRP stands for "Zero Interest Rate Policy," and it refers to a stretch of time — most recently throughout the pandemic — in which the Federal Reserve sets interest rates around 0% and commercial banks are able to borrow money for next-to-nothing. In this episode of Dalton & Michael, we'll talk about some of the downstream side effects we saw during this stretch of time: an explosion of unicorns, a surge of new investors, and the impact it had on the way founders think. We'll share the advice we gave YC founders to brace them for the future, and how some companies made the right move in the middle of an unusual/unsustainable moment. Join us as we look back at how it all played out.
How New Technology Creates New BusinessesWhen a major new technology comes out, huge new opportunities open up for founders that get in on the ground floor. Fortunes were made when the app store came out, when online payments became easy, and when the web itself was brand new. In this episode of Dalton and Michael we'll talk about why this is that moment for AI, who will find those opportunities, and where to look for the people that'll help you find them faster.
When Should You Trust Your Gut?When you're making important decisions as a founder — like what to build, or how it should work — should you spend lots of time gathering input from others or just trust your gut? The answer: it depends. It depends on who you are, what you're building, and what you know. In this episode of Dalton + Michael we talk more about this, and how to know when you should spend time validating and when to just commit.
Why Founders Shouldn't Think Like InvestorsIt's easy to analyze your way out of taking the first step. It's something we see a lot, particularly when founders try to choose what to build based on what they think VCs and investors will like. In this episode of Dalton & Michael, we'll talk about the risks of "thinking like an investor", how to know when you're stuck in this mindset, and how to unlearn it. We'll also cover a short list of things that we've found actually matter when starting a company — it's simpler than a lot of people think.
Building Confidence In Yourself and Your IdeasOne trait that many great founders share is conviction. Dalton and Michael talk about finding confidence in what you're building, the dangers of inaccurate assumptions, and a question founders need to ask themselves before they start trying to sell to anyone else.
Stop Innovating (On The Wrong Things)Startups need to innovate to succeed. But not all innovation is made equal and reinventing some common best practices could actually hinder your company. Dalton Caldwell and Michael Seibel discuss the common innovation pitfalls founders should avoid so they can better focus on their product and their customers.
Should Your Startup Bootstrap or Raise Venture Capital?Within the world of startups, you'll find lots of discourse online about the experiences of founders bootstrapping their startup versus the founders who have raised venture capital to fund their company. Is one better than the other? Truth is, it may not be so black and white. Dalton Caldwell and Michael Seibel discuss the virtues and struggles of both paths.
Do Technical Founders Need Business Co-Founders?Whether or not you need a co-founder is always a hotly debated topic — but going one level deeper, founders often wonder what kind of co-founder they need. It's also common for technical founders to be told by investors and advisors that they would benefit from a co-founder with non-technical expertise in things like business or marketing.
2023
Techno Optimism, ExplainedSocial media often promotes a doom and gloom outlook about our future society. But is that worldview accurate? Dalton Caldwell and Michael Seibel discuss the best ways for founders and aspiring founders to think about weighing optimism and pessimism in their day to day lives.
How To Build A Tech Startup With No Technical SkillsBased on the thousands of companies YC has funded over the years, the biggest common element between all successful startups is having technical talent on the founding team. But what do you do if you don't know how to code? You may think you can get by using no-code tools, part-time consultants, or dev shops to bring your startup idea to life. But that thinking is wrong. In this episode of Dalton & Michael, we'll discuss exactly why that is and why recruiting a technical co-founder is the single biggest way to create value as someone trying to start the next big thing.
How To NOT Get Screwed As A Software EngineerThe stories are true: technical founders (and early technical employees!) often end up with the short end of the stick when starting a company. In this episode of Dalton & Michael, we'll discuss the questions and best practices that an aspiring technical founder should think about — whom to start a company with, and how to think about things like equity split and division of responsibilities. Know what you are worth and act accordingly!
Should You Quit Your Job At A Unicorn?If you're an employee of a late stage company right now, how would you know when it's time to move on vs. time to double down? The fact is there isn't an easy answer — it can really vary from person to person and situation to situation. In this video, YC Group Partners, Michael Seibel and Dalton Caldwell share some suggestions on what sort of things an employee of a late stage startup should be looking for — the good signs and the bad — to best make this decision
Why You Shouldn't Copy Your Tech IdolsDo famous founders give advice they didn't follow themselves? How seriously should you consider the advice of people like Elon Musk, Sam Altman and Peter Thiel? It’s hard not to give advice when you’re successful, but context matters. In this episode, Michael Seibel and Dalton Caldwell dig into why some advice givers might be tempted to say "Do as I say, not as I did" and how we try to avoid doing that within YC.
The Secret That Silicon Valley's Top Investors All ShareDemo day is right around the corner. What do VC firms think of Y Combinator? Dalton and Michael reveal what's really going on behind the scenes with firms like a16z, Sequoia, Founders Fund, and the hundreds of others that invest in YC companies. The data reveals the truth - top investors have stakes in the biggest YC successes. Discover why Y Combinator is a secret weapon for VCs to find promising startups. This video will also teach you to recognize the hidden dynamics that fuel VC motivations so you can make informed decisions when fundraising for your startup.
Does Your Startup Need To Be In San Francisco?Should you and your startup live in San Francisco? Y Combinator Partners, Michael Seibel and Dalton Caldwell, debate their different opinions on whether startups are more likely to succeed in the Golden City or elsewhere. Where do they find common ground?
Will OpenAI Kill All Startups?How will the rise of AI impact startups and entrepreneurs? Join Michael Seibel and Dalton Caldwell for a discussion on the opportunities and challenges AI brings for founders. Through the lens of history and other technological leaps, Michael and Dalton explore the difference between just cargo culting AI versus using it to solve real problems. Will AI usher in a new generation of startups or is this the beginning of the end? These are insights and predictions for startups in this new AI age.
Silicon Valley's Cargo Culting ProblemWhen it comes to building a startup you're never doing it entirely from scratch. Inspiration and ideas can come from a variety of places, including other successful startups. But there's a thin line between borrowing smart ideas and copying them blindly - otherwise known as Cargo Culting. In this episode Dalton and Michael break down the problem with Cargo Culting and offer advice on the right way to draw inspiration from other successful companies.
How Generosity Built Tech GiantsThe core secret to startup success isn't fundraising or growth hacking - it's solving your customer's biggest problems. But most founders are afraid to really understand those problems. What if that fear is holding your startup back? In this episode, Group Partners Dalton Caldwell and Michael Seibel share how companies like Google, Twitch, and Microsoft succeeded by first giving more value than they captured - and how you can too. Learn why your MVP might suck on purpose, how to change your customer outreach, and why you should understand exactly how your customers make money. Because when you solve the right problems, fundraising and scaling become the easy parts.
Secrets You Can Learn From Your CustomersMichael Seibel and Dalton Caldwell discuss how spending real time with your users can unlock insights and growth. Hear the stories of how Airbnb and Brex built billion-dollar companies by forging genuine connections with customers. Learn why having too much money and too many people can actually slow down learning. And discover how to accelerate insight into your product by making your users feel special. Successful startups don’t just build technology – they solve human problems. The key is listening to the people who really matter: your customers.
The Student's Guide To Becoming A Successful Startup FounderIf you're a high school or college student with big dreams of starting your own company, this article is for you. Dalton Caldwell and Michael Seibel, two startup founders who started in the early 20s and are now top investors, sit down to share the hard-won advice they wish they had known back in high school. Whether you're already running your own startup or just have an idea you can't stop thinking about, Caldwell and Seibel will discuss the skills you need to learn now and how to set yourself up for success after graduating school. Their stories will give you a glimpse of what's truly possible at the intersection of ambition and opportunity in in today's world. This is a masterclass in entrepreneurship for the next generation.
How To Earn Customers For LifeMichael Seibel and Dalton Caldwell reveal how startups can gain a competitive advantage by doing something deceptively simple. They share compelling stories of companies that built loyal relationships and achieved success by making personal connections with users. In contrast, they discuss the traps early-stage founders make by trying to emulate big tech. If you want to build a business that customers love and that thrives in the long run, this advice on why caring deeply about your customers is key.
The Hard Conversations Founders Don't Want to HaveIn this video, Y Combinator partners Michael Seibel and Dalton Caldwell discuss the importance of having honest and difficult conversations with startup founders. While having hard conversations can be uncomfortable, Seibel and Caldwell argue that this transparency is essential for founders to grow and ultimately, these experiences help founders have their own hard conversations that they've been avoiding with the people around them.
The Cult of Conformity in Silicon ValleyWhat happens when the unconventional becomes conventional? Michael Seibel and Dalton Caldwell discuss how the startup world has changed from being dominated by outsiders and nonconformists to now attracting more mainstream conformists looking for status and money. They share stories of what the tech scene was like when they were in school - and how radically different it is today. Dalton and Michael offer advice about navigating a world that doesn't always reward nonconformists embarking on risky entrepreneurial journeys. Don't just think different, act different.
The Secrets To Setting Smarter GoalsIf you're looking to maximize your startup's potential, start by setting the right goals. Michael Seibel and Dalton Caldwell provide tips and strategies for setting goals that will help keep you and your new business focused on success—plus provide examples of bad goals to avoid as a startup.
2022
The Truth About Y CombinatorWith the YC S22 batch coming to a close, Dalton Caldwell and Michael Seibel reflect on the recent batch and their experience fundraising. The two group partners also clear up some misconceptions about Y Combinator based on feedback from founders.
The Two Mindsets That Can KILL Your StartupDalton Caldwell and Michael Seibel discuss the qualities that make a founder overly optimistic or far too pessimistic about their startup. Where is the right middle ground?
What Basic Game Theory Teaches Us About StartupsDalton Caldwell and Michael Seibel discuss the problems with zero sum games within tech culture. Is your startup making a positive impact on the world or are your business practices a net negative in society?
Most Important Lifestyle Habits Of Successful FoundersDalton Caldwell and Michael Seibel discuss the best approaches to developing a healthy lifestyle that ultimately helps you run and grow a successful startup. Take care of yourselves out there.
Y Combinator Is Back In PersonDalton Caldwell and Michael Seibel provide an update on the upcoming Summer 2022 batch along with the changes and trends they've noticed in the startup world today.
How To Deal With SetbacksDalton Caldwell and Michael Seibel discuss the best approaches to managing the many setbacks startup founders can face over the lifetime of starting and running a business.
Save Your Startup During an Economic DownturnDalton Caldwell and Michael Seibel discuss Paul Graham's essay "Default Alive or Default Dead." They share strategies to cut your company's burn rate and keep your startup alive to see another day.
Why You Should Leave Your FAANG JobDalton Caldwell and Michael Seibel discuss the struggles of working at FAANG (Facebook, Apple, Amazon, Netflix, Google) and how to strategize leaving a big tech job to become a founder at a startup.
How Future Billionaires Get Sh*t DoneDalton Caldwell and Michael Seibel take a look at Paul Graham's essay "Maker's Schedule, Manager's Schedule" and share tips on how to be more effective and productive on the journey to creating a billion dollar business.
Elon Musk & The Midwit MemeDalton Caldwell and Michael Seibel on the midwit meme, how it applies to startups, and the best example: Elon Musk.
Why Investors Can't Fix Your CompanyDalton Caldwell and Michael Seibel on common pitfalls in the advice from different types of investors and why you, the founder, are ultimately responsible for the success of your company.
Things That Don't Scale, The Software EditionDalton Caldwell and Michael Seibel on software hacks that don't scale. Companies discussed include Google, Facebook, Twitch, and imeem.
What Does It REALLY Mean To Do Things That Don't Scale?Dalton Caldwell and Michael Seibel talk about Paul Graham's essay "Do Things That Don't Scale" and what it really means for founders.
How To Change The World? Get The Small Things RightDalton Caldwell and Michael Seibel talk about the importance of understanding incentives and doing research when it comes to building a world-changing startup.
Simple Products That Became Big CompaniesDalton Caldwell and Michael Seibel talk about OpenSea, Gusto, and the importance of building simple products that solve a real problem.
Where Do Great Startup Ideas Come From?Dalton Caldwell and Michael Seibel talk about where the ideas for Airbnb, Coinbase, and Stripe came from. Then they discuss what you can learn from these founders.
Successful Founders Are OK With RejectionDalton Caldwell and Michael Seibel on the importance of talking to your users, why successful founders are ok with rejection from potential customers, and how protecting your ego by not talking to your users can kill your startup.
Should You Follow Your Passion?Dalton Caldwell and Michael Seibel talk about solutions in search of a problem, whether or not to follow your passion, how to figure out what to work on, and how to motivate yourself.
2021
Understanding Investor Terms & IncentivesDalton Caldwell and Michael Seibel talk about investor terms and incentives.
YC Founders Made These Fundraising MistakesDalton and Michael talk about fundraising mistakes.
Co-Founder Mistakes That Kill Companies & How To Avoid ThemIn the first episode of Rookie Mistakes, Dalton Caldwell and Michael Seibel discuss co-founder mistakes.