Jack's Journal

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Working four jobs

I’m a full blown coffee addict at the moment. The caffeine headaches are real, but it’s what I call a later problem. Why? Because I’m juggling four jobs at the moment.

Job #1: Sales

New Deals → August Pipeline

Between 7/29 - 8/5 we had ~20 firms request a demo/meeting to join our marketplace. For perspective, we usually average 12 a month.

Each demo equals anywhere between $5k-$20k in revenue, 2-3hrs worth of work, and 20% daily energy.

Sales is a balancing act of “don’t bite more than you can chew” vs. “don’t leave money on the table.”

Job #2: Content

Ah yes. The most unforgiving part of my life.

Do you know what it’s like to spend 3hrs editing a video that results in 1,000 views and the next day take 2min to edit another that instantly hits 100,000+ views!? Welcome to content creation.

  • LinkedIn: I post 5-8x a week. It takes 10x longer than you might think.

  • Instagram: Just began a couple weeks ago, it’s the platform I’m most excited about at the moment. Posting 5x a week. (5k new followers in the last 2 weeks!!!)

  • TikTok: It’s a playground. It’s where I learned. Now with 20k+ followers, I know about as much as I did when I began LOL.

  • X/Twitter: Right now my friend Otis and his fiancee are the only ones who like my stuff (thanks guys). But I don’t focus very much here.

Instagram Screenshot

Every post is like a free lottery ticket, keep going until you hit the jackpot.

Job #3: Fundraising

Chatting with VCs, angels, family offices, or any type of investor is one of my favorite parts of the job, but also the most humbling.

They will tear your business apart, find every insecurity, address every hole in your pitch, and challenge every stat you share.

We boostrapped to $100k in ARR before we deposited our first angel check.

Every investor speaks revenue.

Job #4: Operating

Meeting with families, building partnerships, evangelizing the marketplace, running team calls, strategizing growth, tracking progress, managing, hiring, researching, teaching, delegating, explaining…

Build a process. Hire. Train. Repeat.

New website

Individuals & families made it very clear to us in Q2 that they prefer a 1v1 call while accessing our marketplace. So we made it happen.

We launched the new site last Sunday and within 24hrs we were booked throughout the month.

Do things that don’t scale.

Thanks for reading, Habits fam. See you back here next week for more.

-JB