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?

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?

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?