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 left his medical practice after being trained at Harvard and UCLA to become a startup founder. Now, he's solving the silent sleep epidemic alongside his brother. 📚 1,800 Pitch Decks (Free) → deck-database.carrd.co Follow Sahil’s journey: 💼 LinkedIn → linkedin.com/in/sahilchopramd 🚀 Startup → empowersleep.com Follow us: 🔔 Subscribe → youtube.com/@callmehouck?sub_confirmation=1 📝 Newsletter → join.foundingjourney.com 📈 Founder Membership → upgrade.foundingjourney.com 💼 LinkedIn → linkedin.com/in/michael-houck In this conversation we discuss: Founder Mode (00:00) — Intro (01:12) — Becoming a doctor before a founder (02:46) — Convincing his brother to start a company with him (05:08) — Starting a company with your brother (06:52) — Working alongside a complementary co-founder (08:20) — Transitioning to his brother becoming CEO (10:57) — The fundraising process (13:15) — Transitioning from fundraising to building (14:36) — Hiring good people early on (37:37) — Having the right founder mindset (39:03) — Staying even-keeled as a founder (41:17) — Solving your own problems (42:27) — Why sleep is a venture-scale opportunity (43:31) — Importance of a frictionless user experience Health & Sleep (16:46) — Why sleep is so important (18:33) — How much sleep people should get (19:10) — Why people don't prioritize sleep (20:59) — How many people are sleep deficient (23:51) — Sahil diagnoses Michael Houck (32:55) — Defining sleep opportunity vs. sleep (30:48) — The Empower Sleep vision (33:44) — Drive to conquer sleep (35:41) — How broken the healthcare system is Rapid Fire (46:01) — Who is one investor you’d recommend? (47:21) — One thing you'd change about startups? (48:30) — Advice for first-time founders? (48:45) — Something you believe that most disagree with?

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?