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6 Months Jobless Taught More Than 6 Years in Tech - Founders Journey #1

A series on how I'm building 2 tech startups. My weekly brain dump delivered to your inbox on Wednesdays.

Hi friends šŸ•ŗ!

Happy Wednesday evening. Welcome to the Founders Journey Newsletter!

Iā€™m starting a weekly publication that covers what Iā€™m learning while starting a couple software companies. I call it Founders Journey.

First things first, a huge thank you to everyone whose subscribed. Weā€™re at 100 subscribers strong!

My Content AHA Moment

The last 6 months I struggled keeping up with content creation because it wasnā€™t funā€¦. teaching people about product got boring.

Starting a startup and being a PM are not the same. 

Learning how to start a marketplace and a SaaS company at the same time teaches you A LOT. I donā€™t care how many podcasts, books, medium articles, or vc chats youā€™ve had.. IRL experience trumps.

SO. In the spirit of Gary VEEā€™ing some content, Iā€™m documenting my journey and sharing my favorite links & listens along the way.

What you can expect from Founders Journey:

  • Favorite podcasts

  • Favorite articles

  • Challenges Iā€™m dealing with

  • Product updates to give feedback on (just reply to the email)

#1 - Funemployment Provoked Wisdom

Itā€™s been 6 months since I resigned from my day job as VP Product at Delivery Dudes.

Since then I

  1. Turned down offers from a few companies

  2. Traveled Greece for 2 weeks (dope gyros & cheap beer šŸŗ)

  3. Traveled Northern Italy for a week

  4. Launched a live entertainment marketplace with friends

  5. Broke up with my girlfriend of 6 years over FaceTime (NOT THE MOVE.)

  6. Moved into an unfinished cottage in rural Texas (not ideal)

  7. Tried my hand at launching a digital course (felt cheesy - learned a lot )

  8. Launched a SkillShare Course

  9. Iterated on many versions of a SaaS dev tool startup with a best friend

  10. Tried to grow a YouTube channel

  11. Taught myself HTML, CSS, Tailwindcss, Fundamentals of React, and Next.js

  12. Learned the basics of company fundraising (so many books)

  13. Successfully pitched many angels

  14. Wrote several web apps using React

  15. Got back together with my girlfriend (lā€™m lucky šŸ€ )

  16. Had a falling out with my cofounder of the SaaS company ( šŸŽ¢ )

  17. Moved to downtown Austin, Texas ( šŸ˜ )

  18. Started running and strength training more

This six months has taught me more about myself than any other year of my life. Getting out of your comfort zone forces an immense amount of personal growth.

Theres a Japanese philosophy I subscribe to called Igikai.

The basic concept is do something:

  1. You enjoy

  2. Youā€™re good at

  3. You love

  4. You can get paid for

In my case, Iā€™ve always liked building things and being entrepreneurial. Since I was 14 I didnā€™t want to be an employee. Eventually I walked out on my grocery store job to hang up flyers around town offering services of airport pickups (Uber didnā€™t exist), dry cleaning pickup, gardening, you name it. I called it Rent-a-son. I made 10x what I wouldā€™ve had I stayed at the grocery store.

Why do a Startup?

In my previous position as VP Product at Delivery Dudes I was lucky to have a ton of freedom.. If you have a steep growth trajectory you need to find a company or environment that compliments you. 

Over the last few months I tried my hand at a lot of different projects. I said when I quit that I wouldnā€™t work a day for 6 months (thank you Tesla, Square, and a handful of other growth stocks I dollar-cost averaged into over the last 5 yrs).

In my head I thought ā€œIā€™ll take a few weeks then start consulting.ā€ Instead I started producing more content, writing more code, designing more interfaces, building more MVPā€™s and learning the game of fundraising. Iterating on what I wanted to be doing.

ā€œWorkā€ is subjective. Work to me is building someone elseā€™s vision and wealth.

I suppose thats the case too if youā€™re an entrepreneur unless you bootstrap.. but at least youā€™re capturing more of the value.

As an entrepreneur youā€™re creating a vision and executing on it.

I want to create services and products that solve real problems. I got a taste of it as a VP Product and itā€™s addictive.

Thatā€™s why Iā€™m doing startup life. Itā€™s too fun so far. I get to build, and work with like-minded folks.

Being Adaptive

I planned to launch my marketplace apps in July. That got kicked to Septemberā€¦ which got kicked to mid November. Whoops. Adapt and react.

I planned to raise $500,000 for my SaaS startup with my best friend by the end of the year. He ended up taking a full-time gig and bowed out a couple weeks ago. Whoops.

I believe everything happens for a reason. Now I have more of a chip on my should than I ever have.

In the wise words of renowned investor Josh Wolfe (pretty sure he didnā€™t coin it butā€¦)

ā€œchips on shoulders equal chips in pockets ā€œ

Since the founder breakup Iā€™ve been coding more than ever.

Some highlights:

  • Coded up a marketing site for the SaaS co in a morning

  • Coded up a Spotify clone to learn the full stack

  • Modded out iTerm2 (only real ones know the joy)

I adjusted my timeline to deliver an MVP by end of December and raise a seed round of funding by end of Jan.

I am actively looking or a technical cofounder who wants to change the way product teams deliver new features globally.

Treat your Schedule like a Product

I feel like every week I tell my girlfriend:

ā€œI think I finally figured out how to split up my weekā€

I realized this was a bit repetitive when finally one day she said ā€œyouā€™ve said that a lot lately!ā€.. This is a good thing. 

Iā€™m constantly trying to figure out better ways to split my time between the SaaS company which is in idea phase, the marketplace apps which are in private beta, and my personal and social life living in a new city for the first time.

I figured out (the hard way) this summer, that you need to have more balance in your life. At one point I plotted my calendar with 12 hours of different color coded work projects 6 days a week. This ainā€™t healthy. Look at Elon..

šŸ¤œ Related Listens šŸ¤›

I recently found a great podcast featuring Rob Dyrdek (yeah the skater guyā€” bare with me). Rob talks about his week and how he splits it.

7-7-7-3. 

  • 7 hours sleep

  • 7 hours on relationships (friends, family)

  • 7 hours work

  • 3 hours health

Heā€™s crazy though and takes it to the next level by entering it all in a google spreadsheetā€¦

Youā€™re not always going to hit the 7-7-7-3 numbers but theyā€™re great guides to use for your calendar. Right now I am skewing more towards work because I lost my cofounderā€¦ Sleep needs work!

I make time for health by either running or lifting, and I make sure to FaceTime my girlfriend every day.

We dont get the full 7 hrs obviously since we are now in a long distance relationship. When we visit one another I totally turn off work and only focus on her. BALANCE!

If you donā€™t like something, change it

A year ago I created a lot of content about product management on YouTube because I saw other YouTubers making six-figure incomes by producing content.

I jumped on the bandwagon and started churning out content. It didnā€™t feel authentic. I didnā€™t like making the content.

These are just a few things Iā€™ve learned so far. If you enjoyed this do me a favor and forward it to a friend!

I hope you enjoy my Founders Journey story and follow along for more updates on Twitter.