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Founding Journey

Founding Journey

Written by: Michael Houck
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Interviews with world-class startup founders about their unique paths to uncover tactical insights they've learned about how to fundraise, grow, validate, hire, scale, and lead teams while building your startup.

Get full access to detailed takeaways on each episode, additional case studies, and more at join.foundingjourney.comMichael Houck
Economics Leadership Management & Leadership
Episodes
  • How Arjun Mahadevan Raised $1 Million In 2 Minutes
    Apr 2 2025

    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.co


    Follow Arjun’s journey:

    🐦 X → x.com/ArjunMahadevan

    💼 LinkedIn → linkedin.com/in/mahadevanarjun

    🚀 Startup → doola.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
    • (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 founder


    Fundraising

    • (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 batch


    Startup 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 bookkeeping


    Growth

    • (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 customers


    Rapid 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?
    Show More Show Less
    59 mins
  • How Stella Garber Raised $5M To Build An AI Task Manager
    Mar 15 2025

    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.co


    Follow Stella’s journey:

    🐦 X → x.com/startupstella💼 LinkedIn → linkedin.com/in/stellagarber🚀 Startup → hoop.app

    Follow us:🔔 Subscribe → youtube.com/@foundingjourney?sub_confirmation=1📝 Newsletter → join.foundingjourney.com📈 Founder Membership → upgrade.foundingjourney.com💼 LinkedIn → linkedin.com/in/michael-houck


    In 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 Hoop


    Marketing & 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 taste


    Pivoting

    • (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 pivot


    Startups & Launch Tips

    • (29:14) — Transitioning from founder to an early team member
    • (32:38) — Successful Product Hunt launch tips


    Remote 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 team


    Rapid 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?
    Show More Show Less
    59 mins
  • How Sahil Chopra Went from Doctor to Startup Founder
    Jan 17 2025

    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?

    Show More Show Less
    51 mins
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