Why Most Founders Fail: Midday Squares’ Jake Karls on Building in Public

Why Most Founders Fail: Midday Squares’ Jake Karls on Building in Public

For Episode 3, we're joined by Jake Karls, co-founder and Chief Rainmaker of Midday Squares, the chocolate snack company that grew from a tiny condo kitchen in Montreal to more than 10,000 stores across North America. Jake shares why authenticity beats perfection, how building in public helped Midday Squares stand out in a crowded market, and the lessons he learned from multiple failed businesses before finding product-market fit. We also dive into entrepreneurship, storytelling, burnout, hiring, content creation, and what it really takes to build a lasting company. In this episode, we cover: • Why building in public creates stronger customer relationships • The importance of product-market fit before focusing on growth • How Midday Squares went from 50 bars per day to 150,000+ per day • Why authenticity wins in a world full of AI-generated content • How posting online led to fundraising, partnerships, and growth opportunities • The biggest mistake Jake made in his first failed startup • Why founders should focus on their strengths instead of their weaknesses • How to build teams with complementary skill sets • Lessons from burnout and sustaining high performance over the long term • Why the people who stay in the game the longest often win the biggest If you're a founder, creator, operator, student, or anyone trying to build something meaningful, this episode is packed with practical lessons on entrepreneurship, storytelling, resilience, and building a business that lasts. #Entrepreneurship [https://www.youtube.com/hashtag/entrepreneurship] #Startups [https://www.youtube.com/hashtag/startups] #MiddaySquares [https://www.youtube.com/hashtag/middaysquares] #ConsumerBrands [https://www.youtube.com/hashtag/consumerbrands] #BuildingInPublic [https://www.youtube.com/hashtag/buildinginpublic] #FounderStory [https://www.youtube.com/hashtag/founderstory] #ProductMarketFit [https://www.youtube.com/hashtag/productmarketfit] #LinkedIn [https://www.youtube.com/hashtag/linkedin] #ContentCreation [https://www.youtube.com/hashtag/contentcreation] #BusinessGrowth [https://www.youtube.com/hashtag/businessgrowth] #ZeroToOnePodcast [https://www.youtube.com/hashtag/zerotoonepodcast] #StartupAdvice [https://www.youtube.com/hashtag/startupadvice]

AI Will Change 70% of Your Job by 2030: LinkedIn’s CEOO

In this episode, hosts Aashna Doshi & Rayan Dabbagh sit down with Aneesh Raman, LinkedIn’s Chief Economic Opportunity Officer and co-author of Open to Work, to unpack one of the biggest questions of our generation: what happens to work in the age of AI? From his unconventional career journey spanning war correspondence at CNN, speechwriting for President Obama, startups, public policy, and now LinkedIn leadership, Aneesh shares why the future belongs to adaptable thinkers, curious builders, and people willing to embrace discomfort. We explore LinkedIn’s unique view into the global labor market, why 70% of job skills are expected to change by 2030, and how AI is reshaping careers, hiring, entrepreneurship, and the very structure of companies themselves. Along the way, we discuss: * Why the traditional career ladder is disappearing * How AI is changing software engineering jobs * Why storytelling and communication are becoming critical skills * The rise of creators, founders, and entrepreneurial careers * Why “the new resume is the work itself” * How students should think about careers in the AI era * The future of AI agents, human capability, and work * Why handling hard things well becomes a superpower Whether you're a student, founder, software engineer, creator, or someone trying to navigate the future of work, this episode offers a deeply human perspective on how to stay relevant, resilient, and ambitious in the AI era.

AI Will Create MORE Tech Jobs – CEO of Andela Explains Why

In this episode, hosts Aashna Doshi & Rayan Dabbagh sit down with Carrol Chang, CEO of Andela, the global tech talent marketplace connecting companies with top engineers across 135+ countries. From her early work in immigration and public service to scaling global operations at Uber during one of its most turbulent eras, Carrol shares how change management, storytelling, and systems thinking shaped her leadership journey and why she believes AI will create more technology jobs, not eliminate them. We explore how Andela uses AI-driven assessments to match engineers with companies, what “AI-native” developers need to focus on, and why architecture and critical thinking matter more than ever. Carrol breaks down the future of hiring, from human + agent collaboration to task-based work replacing traditional job structures. Along the way, we discuss: * Why junior engineers might actually win in the AI era * The real difference between coding and architecting systems * How remote work unlocks global opportunity * What skills will separate top talent in the next decade * The one leadership lesson she carried from Uber into Andela Whether you're a CS student questioning your major, a founder building in the AI age, or an engineer navigating this shift, this episode is a roadmap for the next generation of work.

Are Dating Apps Dead? How AI Is Changing Love

In this episode, hosts Aashna Doshi & Rayan Dabbagh sit down with Nandini Mullaji, co-founder of Sitch and the personality behind Dini in a Bottle. From her Bombay roots (with a matchmaker grandmother) to Georgetown → McKinsey → VC → Stanford GSB, Nandini shares how she shut down her first dating app, found the right co-founder, and built an AI-powered matchmaking service that people actually pay for. We explore why dating apps miss the mark and what AI matchmaking does differently, the moment she pivoted from a Big Tech career path to founder life, and the lessons she learned from shutting down her first startup. Nandini also breaks down how Sitch blends AI and human judgment, why people overshare with bots (and how that becomes a moat), and the onboarding + verification process behind their pay-per-date model. Along the way, she talks about data points that don’t actually predict long-term compatibility, the challenges (and strengths) of being a woman founder in this space, and the zero-to-one lessons that apply equally to building love and startups. Whether you’re single, curious about the future of dating, or thinking about starting something of your own, this conversation is packed with insights on technology, relationships, and the art of building connection.

Email was broken. We fixed it.

In this episode, hosts Aashna Doshi & Rayan Dabbagh sit down with Nizzy, cofounder of Mail0 and one of the internet’s most popular coding educators turned founder. From making fun, beginner-friendly YouTube tutorials to building an AI-native email client backed by YC, Nizzy’s journey shows how consistency and community can transform side projects into startups. We explore how teaching as a beginner made him a better developer, why “there are no moats anymore” in tech, and how distribution — not just features — is Mail0’s real edge against giants like Gmail. Nizzy also shares how Twitter/X acts as a funnel for YouTube and product growth, why open source has been core to building Mail0, and how remote team rituals like Demo Days keep morale high. Whether you’re an aspiring creator, a developer wondering how to stand out, or a founder curious about taking on incumbents — this episode is packed with lessons on consistency, distribution, and building community-first products.