Founding Journey

Arjun built a $100M startup by helping other founders incorporate and start their own. Along the way he went through Y Combinator and built an audience of over 80,000 people on X and LinkedIn.📚 1,800 Pitch Decks (Free) → deck-database.carrd.coFollow Arjun’s journey:🐦 X → x.com/ArjunMahadevan 💼 LinkedIn → linkedin.com/in/mahadevanarjun 🚀 Startup → doola.comFollow us: 🔔 Subscribe →youtube.com/@callmehouck?sub_confirmation=1 📝 Newsletter → join.foundingjourney.com 📈 Founder Membership → upgrade.foundingjourney.com 💼 LinkedIn → linkedin.com/in/michael-houckIn this conversation we discuss:Founder Mode(00:00) — Intro(04:09) — Fundraising skills applications to life(05:07) — Creating a founder brand(06:35) — How Arjun is thinking about AI(12:07) — Advice to a first-time founder(24:31) — What Arjun took from working at Dropbox(26:35) — Dealing with failure as a 1st-time founderFundraising(01:13) — How to raise $1M in 2 minutes(14:45) — Going through OnDeck & Y Combinator(17:59) — doola’s value prop(21:03) — doola’s pivot during YC batchStartup Strategy & Operations(08:01) — Why doola niched down to E-commerce(10:21) — Why data isn’t as actionable as we think(30:25) — Importance of asymmetric upside(44:08) — How to know when to build vs. partner with external vendors(46:36) — Incorporation(50:38) — Importance of bookkeepingGrowth(32:38) — The content funnel(35:25) — Creating content for systems(37:45) — Content platforms to be excited about(41:09) — Why any problem can be solved by talking to customersRapid Fire(53:23) — Who is one investor you’d recommend?(53:44) — One thing you’d change about startups?(54:29) — Advice for first-time founders?(55:33) — Something you believe that most disagree with?

Stella has worked in startups her entire career. She started previous companies and even got the opportunity to join Trello as an early employee. She scaled with the company all the way through it’s acquisition by Atlassian. She then founded Hoop and raised $5M to solve productivity.📚 1,800 Pitch Decks (Free) → deck-database.carrd.coFollow Stella’s journey:🐦 X → x.com/startupstella💼 LinkedIn → linkedin.com/in/stellagarber🚀 Startup → hoop.appFollow us:🔔 Subscribe → youtube.com/@foundingjourney?sub_confirmation=1📝 Newsletter → join.foundingjourney.com📈 Founder Membership → upgrade.foundingjourney.com💼 LinkedIn → linkedin.com/in/michael-houckIn this conversation we discuss:Trello Journey & Early Growth(00:00) — Intro(01:48) — How Stella became an early Trello team member(03:27) — Marketing changes during Trello’s growth(07:28) — Trello’s marketing success & applications to HoopMarketing & Product Growth(11:07) — Marketing from a user-centric lens(12:45) — Unique approach to organic growth(14:06) — AI’s impact on product growth(15:55) — Product tastePivoting(17:27) — The future of productivity & Hoop(21:32) — Pivoting after ChatGPT’s launch(24:51) — The conflicting pivot advice(26:15) — When to know you need to pivotStartups & Launch Tips(29:14) — Transitioning from founder to an early team member(32:38) — Successful Product Hunt launch tipsRemote Work & Team Dynamics(37:11) — Remote work & 4-day work week(42:08) — Asynchronous remote work(44:41) — “Burstiness”(47:41) — How to create a successful remote teamRapid Fire(52:51) — Who is one investor you’d recommend?(53:28) — One thing you’d change about startups?(55:55) — Advice for first-time founders?(56:34) — Something you believe that most disagree with?

Sahil Chopra, a Harvard and UCLA-trained doctor, pivoted from medicine to become a startup founder focused on tackling the sleep epidemic alongside his brother. He shares his unique journey, emphasizing the challenges and rewards of co-founding with family. The conversation dives into the critical importance of sleep, how many people are actually sleep-deprived, and innovative strategies for improving sleep health. Chopra also discusses fundraising tactics, maintaining a founder mindset, and crafting a frictionless user experience in the sleep tech industry.

Adam Nathan raised $45M at a $150M valuation for his startup, Almanac. But then he realized he needed to pivot…  and he pulled it off. He's now on track to go from 0 - $10M in revenue in just 15 months with the pivoted company, Blaze.ai📚 1,800 Pitch Decks (Free) →deck-database.carrd.coFollow Adam’s journey:🐦 X →x.com/adampnathan💼 LinkedIn →linkedin.com/in/adampnathan🚀 Startup →blaze.aiWant to hear more from Adam? Get Startup Tycoon in your inbox weekly →startuptycoon.comFollow us:🔔 Subscribe →youtube.com/@foundingjourney?sub_confirmation=1📝 Newsletter →join.foundingjourney.com📈 Founder Membership →upgrade.foundingjourney.com💼 LinkedIn →linkedin.com/in/michael-houckIn this conversation we discuss:Intro & Background(00:00) — Intro(01:11) — Shutting down Almanac(04:24) — Starting BlazeFounder Mode(16:54) — Prioritization during hyper growth(24:32) — Knowing when to delegate(30:02) — Not being the "idea guy"(33:48) — Second mover advantage(42:28) — Intentional branding(49:34) — Overbuilding product features(55:53) — How fundraising changes a businessRapid Fire(1:03:41) — Who is one investor you’d recommend?(1:04:25) — One thing you'd change about startups?(1:04:45) — Advice for first-time founders?(1:05:20) — Something you believe that most disagree with?

This is how Luke got a $100,000 investment to drop out of college and turned it into a $27 million startup. He breaks down how to identify and build your own vertical SaaS business too.📚 1,800 Pitch Decks (Free) → deck-database.carrd.coFollow Luke’s journey: 🐦 X → x.com/lukesophinos 💼 LinkedIn → linkedin.com/in/lukesophinos 🚀 Startup → coursekey.com📝 Newsletter → newsletter.lukesophinos.com 📔 Vertical SaaS Bible → verticalsaasbible.comFollow us: 🔔 Subscribe → youtube.com/@foundingjourney?sub_confirmation=1 📝 Newsletter → join.foundingjourney.com 📈 Founder Membership → upgrade.foundingjourney.com 💼 LinkedIn → linkedin.com/in/michael-houckIn this conversation we discuss:Founder Mode(00:00) — Intro (01:18) — Luke's first business(03:32) — Joining a VC firm in college(06:33) — Becoming a Thiel Fellow(11:26) — Dropping out of college & going all in(15:33) — Why traditional education is broken(18:04) — Why founders should target boring industries(19:53) — Building trust(21:04) — When to pivotVertical SaaS(22:46) — Differences between vertical & horizontal SaaS(23:53) — Why vertical SaaS has better opportunities going forward(26:53) — What makes for a venture-scale vertical SaaS product(32:38) — Why vertical SaaS is criticized for not being venture scale(34:30) — AI's impact on vertical software(37:37) — Why Luke is sharing the vertical SaaS playbook(39:00) — The vertical SaaS bible(39:53) — Where to start building vertical SaaS businesses(41:53) — Raising venture funding & debt financingRapid Fire(44:50) — Who is one investor you’d recommend?(45:08) — One thing you'd change about startups?(45:38) — Advice for first-time founders?(46:00) — Something you believe that most disagree with?

Aleksandr helped one person hire an engineer. A few years later, it's turned into a $16 million, largely bootstrapped business.📚 1,800 Pitch Decks (Free) → deck-database.carrd.coFollow Aleksandr’s journey: 🐦 X → x.com/volodarik 💼 LinkedIn → linkedin.com/in/volodarik 🚀 Startup → lemon.ioFollow us: 🔔 Subscribe → youtube.com/@callmehouck?sub_confirmation=1 📝 Newsletter → join.foundingjourney.com 📈 Founder Membership → upgrade.foundingjourney.com 💼 LinkedIn → linkedin.com/in/michael-houckIn this conversation we discuss:Founder Mode(00:00) — Intro(01:07) — Lemon.io founding story(04:15) — How Aleksandr knew Lemon.io was a big opportunity(06:15) — Lemon.io's differentiator(07:49) — Why founders miss opportunities right in front of them(42:00) — Aleksandr’s first 2 businessesRebranding & Growth(09:49) — Intentional rebranding efforts(14:42) — Tactically executing a rebrand(16:25) — Building in public in 2025(18:48) — 2025 social media plan(22:19) — Building in public's impact early on(23:58) — Using Quora as a growth channel(24:22) — 2025's growth channel opportunity(26:34) — Utilizing the podcast growth channel(31:06) — Going all in with early-stage advertisingHiring(34:31) — Making first sales hire(43:50) — The benefit of paid work trials(46:11) — What founders should evaluate when hiring(47:06) — How non-technical founders can evaluate technical talent(48:50) — Laying off employees while growingInvestment(35:54) — The wrong way to take on venture investment(39:38) — Buying out existing investors(40:07) — Why there’s no need to raise more for Lemon.ioRapid Fire(52:58) — Who is one investor you’d recommend?(53:58) — One thing you'd change about startups?(54:41) — Advice for first-time founders?(55:36) — Something you believe that most disagree with?

Pujun Bhatnagar dropped out of Stanford, Harved, and MIT to build startups. He decided to build in an unsexy industry and it worked. He doubled Kintsugi’s valuation to $75M in 3 months.📚 1,800 Pitch Decks (Free) → deck-database.carrd.coFollow Pujun’s journey: 🐦 X → x.com/pujun_ai 💼 LinkedIn → linkedin.com/in/pujun 🚀 Startup → trykintsugi.comFollow us: 🔔 Subscribe → youtube.com/@callmehouck?sub_confirmation=1 📝 Newsletter → join.foundingjourney.com 📈 Founder Membership → upgrade.foundingjourney.com 💼 LinkedIn → linkedin.com/in/michael-houckIn this conversation we discuss:Kintsugi(00:00) — Intro(00:57) — What Kintsugi does & why it's successful(14:22) — What Kintsugi meansFounder Mode(03:15) — Why Pujun did an "unsexy" business(09:40) — AM frequency vs. Pujun's FM frequency(12:29) — What happens to ambition when success comes(26:20) — Pujun's mindset shifts over time(32:20) — Pujun's toughest situation with co-founders(59:10) — Dropping out of academia 3x(1:07:20) — What Pujun does when not performing at his best(1:10:00) — Pujun's spicesAI & Technology(05:36) — What problems AI can solve(19:44) — Successfully building AI PLG(21:44) — The future of AI models(51:14) — Differences between the ML & LLM gold rush(54:46) — How to identify AI snake oilGrowth & Strategy(17:06) — Focusing on building good software(24:31) — Tradeoffs that come with scale(34:51) — Having conviction & discipline(36:11) — Who Pujun & Kintsugi looks for in teammates(38:09) — Doubling valuation in 3 months time(42:04) — Optimizing for minimal dilution(43:53) — Ruthless prioritization when scalingRapid Fire(1:12:09) — Who is one investor you’d recommend?(1:13:33) — One thing you'd change about startups?(1:16:22) — Advice for first-time founders?(1:16:55) — Something you believe that most disagree with?

This is how Tibo Louis-Lucas built a new startup every month... until one took off and turned into a $10 million exit.📚 1,800 Pitch Decks (Free) → https://deck-database.carrd.coFollow Tibo's journey: 🐦 X → x.com/tibo_maker 🚀 Website → tmaker.ioFollow us: 🔔 Subscribe → youtube.com/@foundingjourney?sub_confirmation=1 📝 Newsletter → join.foundingjourney.com 📈 Founder Membership → upgrade.foundingjourney.com 💼 LinkedIn → linkedin.com/in/michael-houckIn this conversation we chat about:Founder Mode(00:00) — Intro(01:24) — Being a venture-backed founder(02:41) — Learnings from early business failures(24:00) — Identifying scalable business opportunities(33:20) — Goal of getting 5 companies to $100k MRR in 3 years(41:35) — How to unlock different versions of yourself(43:02) — Identifying opportunities while building multiple companiesGrowth & Scaling(05:14) — The advantage of quickly shipping(08:36) — Pros and cons of building in public(10:28) — Alternatives to building in public(11:24) — The moats that exist today(15:31) — Utilizing micro-influencers for growth(37:56) — Keeping 2-person companies at scale(39:18) — Working alongside a complementary co-founderProduct & Acquisition Strategy(12:55) — Platform risk(18:32) — How founders can learn to kill products(20:35) — Outsourcing to external developers(21:57) — Buying small products(25:26) — Deciding how much to invest into micro-acquisitions(27:47) — Buying & selling assets rather than companies(30:42) — Buying a tool to compete with the newsletter giants(36:46) — AI’s unique software enablement(44:08) — Deciding when and how to sell your company(48:10) — How to decide how and whom to sell your company toAdvice & Insights(49:04) — Founder Tips for Negotiating Deals(49:57) — Bootstrapping vs. raising VC(52:08) — The future of SaaS(55:58) — Taking a job after being a founder(58:21) — Founders don’t know when they need to quitRapid Fire(59:18) — Who is one investor you’d recommend?(59:46) — One thing you'd change about startups?(1:00:20) — Advice for first-time founders?(1:00:51) — Something you believe that most disagree with?

This is how Adam raised over $3 million for his hiring startup Pangea.app, and why he won’t need to raise again.📚 1,800 Pitch Decks (Free) → deck-database.carrd.coFollow Adam's journey: 🐦 X → x.com/the_pangean 💼 LinkedIn → linkedin.com/in/adamalp 🚀 Startup → pangea.appFollow us: 🔔 Subscribe → youtube.com/@foundingjourney?sub_confirmation=1 📝 Newsletter → join.foundingjourney.com 📈 Founder Membership → upgrade.foundingjourney.com 💼 LinkedIn → linkedin.com/in/michael-houckAccelerators & Fundraising00:00 — Intro01:10 — Incubators/accelerators05:56 — YC application experience1:03:11 — Fundraising isn't the goal1:07:02 — When you don’t get immediate fundingFounder Mode:09:42 — The founder mindset & validation38:19 — Tough decisions & losing customers43:22 — Knowing when to change course46:07 — When you're too niched down59:01 — What gave Adam conviction to go all in1:10:51 — Why founders should explore stoicismProduct Development14:55 — MVP Versus SVP20:53 — Getting to #1 on Product HuntCommunity & Growth22:14 — Product Hunt launch impact25:18 — Long-term growth strategies26:45 — Getting customers through ChatGPT30:17 — SEO & AI/LLMs34:49 — Growth channels & niching down49:27 — Why community is keyFounding & Leadership Insights50:48 — NYC Founders Club52:17 — Vision for the future55:46 — Focus areas when hiringRapid Fire1:12:29 — Who's an investor you'd recommend?1:13:40 — One thing you'd change about startups?1:14:22 — Advice for first-time founders?1:14:35 — Something you believe that most disagree with?

Discover how successful founders leveraged their networks to raise $450 million for their startups. They share insights on turning early investors into loyal customers and the power of community in fostering growth. Hear about innovative community-building strategies, like hosting engaging events and using celebrity partnerships. Learn about the 'big small big' product development framework that balances vision with actionable feedback. This lively discussion uncovers the essential role of authenticity and connection in the entrepreneurial journey.