Hey there! Welcome to the Independent Money newsletter 👋 We’ll be exploring the fascinating lives of our favorite entrepreneurs. We’re taking a closer look at their backgrounds, careers, and financial journeys.

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We had the chance to chat with Chris Bakke, the entrepreneur behind Laskie (acquired by Twitter/X) and Interviewed (acquired by Indeed). Chris opened up about his journey building companies and sharing lessons on entrepreneurship, funding, and money management he learned along the way. His straightforward advice is perfect for anyone looking to dive into the startup world or just curious about how he made it happen.

I’m Chris Bakke - founder of Laskie (acquired by Twitter/X in 2023) and Interviewed (acquired by Indeed in 2017). I’m spending lots of time online, so you can follow along here.

Entrepreneurship

What’s one thing you wish you knew before becoming an entrepreneur?

I wish I had actually started sooner. I started my first company at 25, but feel like I wasted countless hours reading books and articles about starting and operating companies. My experience was completely different from anything I’ve ever read about, and the only way you’re going to figure it out is by jumping in and forcing yourself to keep your head above water. 

Did you start creating content to grow your company, or did you start your company in response to your audience's growth?

I started posting on Twitter in late 2019. I was a bored, acquired founder at a pretty big company, looking to reconnect with the tech world. I spent 6 months replying sarcastically to obnoxious VC tweets, and then started posting my own content in mid-2020. When I started a company in late-2020, I discovered that my sassy tweets were driving real customers, so I got a lot more deliberate about posting every day.

What’s your opinion on funding vs bootstrapping a business? Did you raise capital?

The two companies I’ve sold both raised capital from angels and VCs. But I also own companies like Napa (a ghostwriting service for founders and executives) that were very successfully bootstrapped. The default for more businesses should be to not raise capital and fund your business from customers.

What’s one tip for someone who’s founded a company and is hoping to exit?

Ali Rowghani told me something that changed my trajectory before I sold my first company. He said, “For most companies, there are only 20 or 30 companies that might possibly buy you some day. Because way more ‘successful’ companies sell versus go public, you’d be wise to build relationships with all 20 of those possible acquirers early.” As a result, we built great, proactive relationships with people at Indeed and Twitter (and dozens of other companies) before we sold.

Money

What’s one money tip you live by?

If you want to have lots of money, you should over-optimize on making more money versus saving. Big wins in my life have always come from being a founder or an early employee with lots of equity upside.

What is your current savings and investing stack/portfolio (i.e any retirement accounts, emergency fund, etc)?

My portfolio is pretty boring. Per my own advice above, my career of starting companies is high-risk, and that’s where I want to optimize my time. That means on the savings and portfolio side, I’m fine with lower-risk. I’m not chasing 40% annual returns: I’m just trying to not lose money, not over-pay in fees, and earn a solid return. Our family’s portfolio is something like 5% cash, 15% real estate, 55% public stocks (almost all through index and mutual funds), 20% private companies (as an LP in large VC funds), and 5% private companies (directly as an angel investor).

Looking for a more automated way to manage your portfolio? Carry’s Robo-Advisor offers a range of investment strategies to suit different risk levels and objectives.

After getting acquired, what’s one thing you learned or wish you knew about taxes?

I knew nothing about taxes after selling my first company. It was pretty regrettable looking back: millions paid in taxes with few questions asked. Selling a company is such a chaotic whirlwind that the last thing on your mind as a founder is, “how do I lower my tax burden here?” Good VCs and lawyers who can help point you in the right directions post-acquisition are really helpful to have.

We exist so you can focus on what matters most, growing your business — that’s why we created a course with 25 strategies to save on taxes.

To learn more about Chris Bakke and stay connected, you can find him on X, on LinkedIn, or check out his newsletter.

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If you want more resourceson building wealth as a solopreneur/entrepreneur, check these out:

• The Solo 401k handbook

• The Roth IRA handbook

• The Self-Directed IRA handbook

• The Guide to Paying Less in Taxes

• What is a Solo 401k?

• How to Open a Solo 401k

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