Shows
Bootstrapped GiantsMotorboat Leadership vs. Sailboat Leadership[00:00:00] Intro – Jesse hints at a personal and professional transition [00:00:27] Jesse’s life update – spiritual journey and post-Japan reflection [00:01:30] The Motorboat vs Sailboat leadership metaphor explained [00:02:51] Internal conflict: fear of letting go and team dependency [00:04:03] Overwhelm from managing multiple businesses – “a company per day” schedule [00:04:48] Inspiration from a friend who only talks to CEOs – true sailboat mode [00:05:24] Every leader needs both motorboat and sailboat energy [00:06:09] Andrew’s emotional reaction to Jesse pulling back from involvement [00:07:12] Jesse’s evolving role – from fractional president to clearing Slack overload [00:08:15] What Jesse wants to focus on – coaching vs tac...2025-07-1141 min
The Heart of EntrepreneurshipIs Spirituality the Missing Key for Founders?You're Not Your Inner Voice: Meditation, Spirituality, and Mental Clarity for Founders✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS:https://bootstrappedgiants.com/join✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter...00:00 – Jesse introduces the topic: spirituality for entrepreneurs01:00 – What does spirituality actually mean (and why should you care)?04:00 – You're not your thoughts: the voice in your head isn’t you06:00 – The meditation misconception: you don’t have to quiet your mind08:00 – Science vs. spirituality: where they’re already merging10:00 – What meditation really trains: non-reactivity13:0...2025-07-0146 minBootstrapped GiantsClose - Focused CRM does $50 million a year[00:00:00] Intro – Andrew sets up the conversation: sales reluctance, AI, and CRM evolution[00:00:47] Steli explains Close's positioning: high-communication CRM for salespeople[00:01:41] Revenue milestone: Close is on track to hit $50M this year[00:02:36] Bootstrapping vs. fundraising: why Close chose profitability over VC[00:04:01] Why staying small and focused is their competitive advantage[00:04:51] Competing with giants: don’t out-fund, out-focus[00:05:31] The power of saying no and maintaining a narrow product scope[00:06:52] Product-led growth: Close doesn’t rely on integrations to win customers[00:07:48] Focusing on deep communication use cases sets Close apart[00:08:51] Why they resist chasin...2025-06-1849 minBootstrapped GiantsHe's controlling ChatGPT responses[00:00:36] Intro: ChatGPT as a traffic driver and Chirag’s early insight[00:01:48] Revenue Numbers and Profitability of Taco[00:02:24] Personal investment strategy and non-AI assets[00:03:36] How Chirag uses AI agents to replace writers and boost efficiency[00:05:42] What makes Taco a true AI-powered agency[00:07:03] Tracking brand rankings inside ChatGPT and Perplexity[00:08:33] Tools used to measure AI visibility and rankings[00:09:18] How to rank higher in AI search engines like GPT and Perplexity[00:10:30] Paid placement strategies in high-authority sites to boost AI visibility[00:11:06] Why AI search traffic converts better than Google[00:12:36] Chirag’s backstory: disc...2025-05-1350 minBootstrapped Giants1440 is a Bootstrapped Giant[00:00:00] Quick Montage (Growth, Grit, Vision, Revenue, Meaning of 1440)[00:00:36] Intro: Why 1440 is Different[00:01:48] Revenue Numbers and Profitability[00:02:24] How They Funded Without Venture Capital[00:04:48] How Big Can an Email Newsletter Get?[00:05:15] Why They Ignored Advice to “Go Niche”[00:06:09] 1440’s Thesis: Inch-Deep, Mile-Wide for the Intellectually Curious[00:08:24] Tim’s Previous Startup: When in Rome (Failure Story)[00:11:15] Lessons on Unit Economics and Why When in Rome Failed[00:15:09] Why Email Newsletters Are Such Great Businesses[00:16:03] Inspirations: Sam Parr, Morning Brew, and the Hustle[00:18...2025-05-0149 minBootstrapped GiantsI Built 4 AI Agents in 2 Weeks – No Code! [00:00:00] Introduction [00:00:45] Early Adoption of Generative AI & GitHub Copilot [00:01:30] Discovering How Code Comments Improve AI Suggestions [00:02:33] Skepticism About AI Hype & Fear of Being Left Behind [00:04:03] Seeing a YouTube Tutorial That Unlocked Building a RAG Agent [00:05:06] Building His First Agent in One Week (and Feeling “Bad at AI”) [00:07:03] From 1 Agent to 4 Agents, Focusing on Small Single-Purpose Tools [00:08:15] Live Business Use Case: The “Mutual Intro” AI Agent [00:09:45] Benefits of Ranking Contacts & Saving Significant Human Time [00:11:15] Attempt to Build a Large, All-In-One Agent & Its Failures [00:14:03] Compounding Error With Multi-Step AI Workflows [00:16:57] Conclusion: Why Single-Purpose A...2025-03-1030 min
Startup Stories - Mixergy#2273 What happened to our partnership?Before I partnered with Jesse Pujji, we were buddy-buddy. Texting all the time. When we got started, we got excited about the world of possibilities for our company.
Now? Something is missing.
I asked him about it. And about where he put his money, why he’s not launching more companies now, what he’s building with AI, and more.
Jesse Pujji is the founder of Gateway X, the venture studio. Jesse & Andrew are building Bootstrapped Giants, a resource for ambitious, unfunded founders.
More interviews -> https://mixergy.com/moreint
Rate this interview -> http...2025-03-0500 minBootstrapped GiantsI found my zone of genius[00:00:00] Intro & Evolving Work Relationship[00:01:03] Balancing Andrew’s Creative Side vs. Business Demands[00:02:06] Integrating Different Approaches from Teammates[00:02:33] Identifying and Staying in Your “Zone of Genius”[00:04:03] Tasks That Energize vs. Tasks That Drain[00:05:06] Struggle With First Drafts & Delegation[00:06:09] Committing to Genius vs. Excellence[00:07:12] “Heroing” & Taking 100% Responsibility[00:09:36] Asking for Help Without Overburdening Others[00:12:18] Intermittent Fasting & Energy Management[00:13:57] Drive to Prove Oneself & Self-Awareness[00:17:06] Pinpointing Andrew’s True Strengths[00:19:03] Jesse’s “Themed” Workdays & Finding Balance[00:24:00] Considering Bigger Moves: M&A vs. New Startups[00:29:18] AI Opportunities & How to Experiment Quickly[00:32:15] Jess...2025-03-0345 min
If you see this contact Andrew: andrew@mixergy.comJesse-Pujji-on-Mixergy-0227252025-02-2746 minThe Heart of EntrepreneurshipWhy You Unknowingly Resist Love, Joy, and FulfillmentMost people think they struggle with fear or failure. But the truth is, we’re often more afraid of love, joy, and being fully seen.In this episode, Dave Kashen, Jesse Pujji, and Andrew Warner uncover the hidden ways we resist appreciation, connection, and fulfillment—without even realizing it. They break down why receiving acknowledgment can feel so uncomfortable, especially for high achievers, and how this subconscious resistance affects success, relationships, and self-worth.Jesse shares a powerful story about a leadership retreat that started as an awkward exercise and transformed into one of the most emot...2025-02-1249 minThe Heart of EntrepreneurshipThe Secret to Creating Your Dream Life and Business in 2025What if the key to creating your dream life and business isn’t about working harder—but about taking radical responsibility for your entire experience, including the belief that it has to be difficult?In this episode, Jesse Pujji, Dave Kashen, and Andrew Warner reveal how entrepreneurs unknowingly create their own overwhelm by holding onto limiting beliefs about struggle and success. They explore why resistance to emotions leads to suffering, how blame keeps you stuck, and why reframing responsibility is the ultimate power move for building a life and business you love.You’ll walk away w...2025-01-0651 minThe Heart of EntrepreneurshipHow Emotions Are Your Decision-Making CompassWhat if the emotions you’ve been avoiding are the key to making better decisions and unlocking your true potential?In this episode, Jesse Pujji, Dave Kashen, and Andrew Warner dive into how emotions like fear, anger, and sadness can guide you to clarity and alignment—if you let them. They explore why resisting emotions creates stress and confusion, while embracing them leads to better decisions, deeper flow, and authentic success.Discover how to stop reacting impulsively, process emotions effectively, and use them as a compass to navigate your entrepreneurial journey with greater ease and fulf...2024-12-3156 min
Business Newsletter RecapEpisode 004 | Bootstrapped Giants, The Sellout Newsletter, MGMT PlaybookEpisode four brings you insights from 3 top business newsletters:-Jesse Pujji shares his most important sales metric in the Bootstrapped Giants newsletter.-Luke Tengstrom shares lessons from Black Friday 2024 and how you can improve your sales during Cyber Week 2025 in The Sellout Newsletter.-We get a unique perspective on leadership and return-to-office mandates in the MGMT Minute newsletter written by Dave Kline.Here are the links to the newsletters and people mentioned in the show:Bootstrapped Giants Newsletter Signup...2024-12-2313 minThe Heart of EntrepreneurshipOutperform Yourself By Breaking Your Upper LimitNo matter how big your goals are or how much you’ve already achieved, you might have an 'upper limit problem' quietly holding you back.In this episode of The Heart of Entrepreneurship, Jesse Pujji, Dave Kashen, and Andrew Warner dive into the hidden barriers that limit success—even for high achievers. Together, they explore how unconscious beliefs and self-sabotage can prevent you from reaching your potential. They share practical strategies for breaking through these limits, discovering your 'zone of genius,' and designing a life that balances fulfillment with success.If you’ve ever...2024-12-1549 minThe Heart of EntrepreneurshipThe Limiting Stories Entrepreneurs Tell Themselves—And How to Let Them GoEntrepreneurs often chase success by pushing harder and striving for more, but what if the real key lies in rethinking the stories we tell ourselves?In this episode, Jesse Pujji and Dave Kashen share practical exercises to help entrepreneurs separate facts from narratives, freeing them from the things that hold them back––like guilt, regret, and burnout. Joined by Andrew Warner, they dive into the challenges of letting go of old beliefs, embracing the present, and finding fulfillment beyond the relentless pursuit of 'bigger and better.'In this episode––Jesse, Dave, and Andrew ha...2024-12-0247 minThe Heart of EntrepreneurshipWhy We're Doing This PodcastJesse Pujji sold a big piece of his company, Ampush. He should have felt "safe" and happy and more productive.It didn't work.He hired Dave Kashen to coach him.That was a huge unlock. It led him to build multiple companies, have a happier family life and embrace his love of teaching.This podcast shows why that happened. And why they're launching a new podcast with the word "heart" in it, even though it's terrible for SEO. I mean really, which entrepreneur is searching the podcast app for the word "...2024-11-0548 minBootstrapped GiantsWe launched a $40k/month newsletterIn this episode: how we launched our newsletter, Bootstrapped Giants.Presented by: Superhuman, the email app that gets us to inbox zero fast, helps us sell more and enables us to collaborate.Time stamps:[00:01:03] Why start the Bootstrapped Giants podcast? [00:01:26] Can you introduce yourself briefly? [00:04:03] Should we use clickbait titles? [00:05:06] How do you handle self-doubt? [00:09:36] Would you refund disappointed sponsors? [00:13:03] What's the human element in business? [00:17:33] What's the Bootstrap Giants business model? [00:20:24] How much revenue from ads? [00:24:27] What is your growth strategy? [00:27:45] Why is private equity be...2024-08-1053 minBootstrapped GiantsE00: Why can't Andrew start this podcast?We recorded 4 episodes and Andrew hasn't posted 1. Why not?2024-08-0243 min
Confessions of a B2B EntrepreneurJesse Pujji Reveals How He’s Building His HoldCo (Gateway X)Jesse Pujji LinkedInJesse Pujji TwitterAndrew Warner LinkedInAndrew Warner TwitterTinuiti x Ampush websiteGateway X websiteGrowth Assistant websiteBootstrapped Giants podcast and newsletterCheck out our awesome sponsor, Fame, they start and grow the world's most profitable B2B podcastsConfessions of a B2B Entrepreneur is handcrafted by our friends over at: fame.soCheck out our five most downloaded episodes:How To Start A Movement with David Heinemeier Hansson of 37signalsChris Walker Rants On Dark Social, Creating Demand & Company BuildingCEO Spends 70% Of Time On His Personal Brand? Guillaume Moubeche Shares AllOLD WAY/NEW WAY with Adam Robinson...2024-08-0133 min