$90k on business roulette


I’m addicted to gambling. Business is my game of choice.

Here are some rules that I play by:

  1. Don’t die. Stay alive long enough, and you’ll eventually win. Never bet the house.
  2. Take asymmetric bets. Every bet should have higher upside than downside. Heads, I win. Tails, I don’t lose much.
  3. Everything is a bet. You can bet with money, time, attention, effort, etc.

As a reminder, last week we discussed the 6 failed projects over the past 19 months before I finally built a working business and went full time on it—A Team Overseas.

I’ve put up over $90k from our personal funds.

My approach could be boiled down to Explore and Exploit:

  • Explore: Make bets until you find one worth doubling down on.
  • Exploit: Double down where the deck is hot.

Explore — 6 projects before A Team Overseas

Total spend = $30k (Dec 2022 - Sep 2023)

Major points of spend:

  • Contractors: $10k
  • Coaching: $1.6k
  • Legal: $2k
  • Software: $5k
  • Acquired pre-revenue product (F me): $10k

Contractors and coaching were the most valuable ways to spend my money during this time.

I paid a business coach via Commit Action and an executive assistant (EA) during this time. I still work with the same EA, Dane, today. Shout out to her.

Dane would help me with initial market research for new ideas, make lead lists, hold me accountable, and more.

My business coach talked to me about getting through the challenges of a new business and helped me understand my patterns. We spoke about similar things last week, like crawling into the comfort of code.

Both of these hires helped me build and maintain momentum.

I always believed the biggest risk to my business success was me. So it makes sense to spend money de-risking me.

Exploit — A Team Overseas and beyond

Total spend = $137k (Oct 2023 - Jun 2024)

Major points of spend:

  • Contractors: $90k ($20k to people who haven’t worked out)
  • Learning/Communities: $8k
  • Sales and marketing $8k
  • Legal: $3k
  • Software: $12k
  • Hardware: $12k

I hesitate to say we’re in the exploit phase now. Because:

  1. Within A Team Overseas, we’re still exploratory. We’re testing new ways to get new clients, we’re hiring former competitors to speed up our learning curve, etc.
  2. “Exploit” is not something we want attached to our brand… you know.. where we help people work with talent at a fraction of the cost.
    Disclaimer to make myself feel better: Our EAs get a big raise to join us from other agencies. They choose to work with us over going direct to clients.

$137k is a lot of money. Most is from revenue earned, but around $60k is from personal funds.

I didn’t just wake up and say, “I’m gonna dump $60k into all this.”

It’s happened over time as we’ve progressed.

I lay out a bet:

Can we hit X goal by Y date with Z resources? If yes, would I put my money on it?

Every time we’ve successfully hit a previous bet, I set the next one with the appropriate goal, timeframe, and resources.

To go full-time, the bet was:

Can I double my business and start paying myself within a year if I go full-time? If yes, would I put my money on it?

The answer: Yes and yes.

So I quit my day job and now I’m working full-time.

Addicts Make Sacrifices

Continuing to place bets can lead to difficult sacrifices though.

For us, taking this full-time bet meant selling our home.

My wife and I literally got married in that house.

Our son spent the first 2 years of his life in that house.

It was a nice single-family house with a backyard for our dog to run around in, nice neighborhood where kids played outside, it was close to family, and had everything.

We thought we’d be there forever.

But we let it go to decrease expenses and continue doubling down on a progressing dream.

There’s some personal guilt here. Putting my family through this and all.

Luckily, my wife is supportive and enjoys our new condo life.

Takeaways

  1. Watch your costs. Random software adds up. Use accounting tools like Puzzle.io or Quickbooks. Review quarterly and cut what you don’t need.
  2. Spend on what matters. Pay for data sources like Apollo to find and reach customers. Hire help for momentum. Don’t operate scared.
  3. Hiring is hard and high stakes. For small teams, each hire is a big percent of your team’s talent. Don’t let bad hires poison your team’s performance bar. When you inevitably hire poorly, fire fast.
  4. Don’t acquire pre-revenue products...cause F me, right?

Next week, I'll start sharing more things that I find interesting. Anything from:

  • Cool podcasts and takeaways I've heard.
  • How we're using AI within A Team Overseas.
  • Tools and snippets that I use.
  • How the founder of the Four Seasons, Isadore Sharp, is one of my biggest inspirations for A Team Overseas.
  • How I'm letting go of some client-facing responsibilities.
  • More

Any of these ideas seem interesting to you? Let me know and I can prioritize it!

Bet with balls,

Kevin Galang

Kinda Cool by Kevin Galang

This weekly newsletter is for the interesting and interested. I share my journey building my business while also sharing new AI tools, podcasts, and other things I find.

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