$27,577/mo in passive income from a lifestyle business: "My partner jokes that I’ve been trying and failing to run out of cash."

35-year-old Tamir Bashkin has never had a job. Instead, he built a passive income through lifestyle businesses and a hands-off investment strategy.

Let's take a peek at his finances.

The search for passive income

When Tamir was in the army, he stumbled upon Tim Ferris’ 4-Hour Work Week and fell in love with the concept.

Of course, he couldn't implement it then, but he kept it top of mind. And, after leaving the Israeli military intelligence, he spent most of his twenties figuring out how to generate $10k/mo passively.

He looked for high-leverage, low-cost moves and avoided the dollars-for-hours trap. He was trying to build a lifestyle business, after all. He wasn't interested in grinding, whether that be with a "hardcore" startup or hourly freelance gigs.

Your business should work for you — not the other way around. Always think, "How is this serving me?"

He achieved his goal in his early 30s with a business called Adelante.

Creating lifestyle businesses

Adelante is a Zendesk consultancy with a productized service that helps companies set up their Zendesk in 7 days or less. Within that service, he also helps with implementation and expansion deals.

But he didn't stop there with one successful lifestyle business.

ClearSight is a newly-launched cybersecurity tool that maps a company's third-party integrations, security settings, and accounts. It helps hands-on chief information security officers monitor and fix any admin mistakes in their SaaS security configuration in real-time.

And Thank You GPT is a no-code — even though he knows how to code — tool that uses OpenAI to identify and solve “thank you messages” for Zendesk, Gorgias, Salesforce, and Intercom.

No code allows me to test ideas within 30 days. Then, I only work on the ones that can become viable businesses.

Now that Thank You GPT has some initial traction and he knows what he's building, though, he's considering moving it to code. He says he'll be able to make it more cost efficient that way.

Revenue from three lifestyle businesses

Here's what he's bringing in:

• Thank You GPT revenue: $2.58k MRR

• ClearSight revenue: $0 (just launched)

• Adelante revenue: ~$25k

• Founder pay: $4k/mo

• Business bank account: ~$250K

• Personal bank account: ~$5k (the "bare minimum" for a few months of backup cash if the business fails)

Adelante has some recurring revenue through affiliate deals and advisory retainers, but it's mostly one-time payments. Thank You GPT's revenue, however, is recurring.

He keeps $250k in his business account because he's looking for investment opportunities and wants cash available for quick decisions. In the meantime, his money is working for him. It's invested in a cash-based mutual fund that returns 8% — or $20k — annually.

As for that $5k in his bank, it isn't much, but it ensures that he can cover unexpected costs. And it gives him cushion and runway in the event that Adelante suddenly goes out of business.

Worst case scenario, he can also take money from Adelante's substantial account. And most of his investments are easily liquidated if necessary. So he doesn't see any reason to keep more in his savings. He'd rather invest it.

I try to ensure that every dollar I have is working to create more money.

Know your tax system

A company is defined by distributing profits to the owner, so ensure you’re paying yourself first and foremost.

Despite having solid revenue, Tamir only pays himself $4k/mo. That's because it's the best threshold for taxes in Israel — any more than this, and his taxes would go up.

But the way he looks at it, he's paying himself $10k/mo because he puts $6k/mo into his business savings and keeps it there for the future, and removes it when taxes conditions are favorable.

It pays to understand your tax system.

Spending where it counts

Here are his monthly business expenses:

• Salaries and freelancers: $7k-10k

• Office rent and utilities: $500

• Software and tools: $1.5k

• Content creation/copywriting help: $700

• Miscellaneous (travel, supplies, accounting etc.): $2.5k

Tamir here tries to keep costs low where he can, but he says you shouldn't get carried away. You need to spend money to make money.

Sometimes, you need to spend twice as much as you’re spending now to earn ten times more.

Keeping costs low

Here are his monthly personal expenses, all of which are split between him and his partner.

• Housing: $2k

• Adopted 10-year-old husky's medical expenses: $300

• Misc (food, restaurants, transportation): $1.2k

As you can see, he gets by (and then some) on $4k/mo. In Israel, the mean income is $3k/mo before taxes, so he does well for himself, even without taking the other $6k/mo into account

Make an investment in time off

Tamir is trying to keep his monthly expenses low, but he doesn't skimp on travel. He takes a week off every quarter to travel somewhere in Europe — sort of a business/pleasure trip. He unplugs and focuses on thinking and planning his next moves.

I’ve had some significant breakthroughs in my travels. It’s a good opportunity to recalibrate and ensure I’m on track to reach my goals.

Usually, he goes to Italy since he has friends there. And he spends his days eating ice cream and either writing, hiking, or thinking.

Oh, and then there's the sushi. While he admits that Italy might be an odd place to splurge on sushi, he can't get enough of Milan's fresh, all-you-can-eat sushi for €15-25.

Self-taught financial literacy

Sushi notwithstanding, you might be getting the sense that Tamir has a good head on his shoulders. He knows his finances. But that wasn't always the case.

His parents had money, so he never missed out on anything, but he says they didn't manage it well. They didn't invest it because they lost faith in the financial system after going through the crashes of 2000 and 2008. And now, they're having difficulty retiring.

As a result, Tamir didn't get a financial education when he was young. But, thanks to the can-do attitude that he picked up in the military, he learned everything that he needed to know on his own by reading voraciously.

He says that having to figure it out on his own gave a greater sense of financial responsibility, and he's grateful for that.

Sticking to the S&P 500

Tamir started investing in 2018, putting everything into the S&P 500. At the time, he put it all into VOO, which focuses on S&P 500 stocks. But he recently switched to VUAA because, as a non-US resident, investing in US-listed ETFs is not viable due to dividend taxes.

Even his IRA pension account, to which he contributes $1200/mo, uses the S&P 500.

I don't care about stock diversification, bonds, etc. My investments are conservative and I don't want to overcomplicate them.

He landed on this approach after doing extensive research and reading books like A Random Walk Down Wall Street and If You Can. The latter actually suggests a different asset allocation, but it's his favorite finance book anyway. He says it captures pretty much everything you need to know on the topic.

So far he's seeing about a 60% return on his investments. He says this is the right choice for him because he doesn't anticipate needing the money for a few decades. He sees it as a good long-term, set-it-and-forget-it investment.

I’m trying to get rich slowly over time. The goal of the index funds is to provide me with the financial independence and funds to go through life comfortably.

Passive investing

Tamir isn't into individual stocks because he can't spare the time to track them. After reading The Intelligent Investor, what stuck with him was that the difference between a passive and active investor is only the amount of time they devote to researching stocks.

And as with his business, he likes a passive approach.

The same applies to crypto. Plus, he just doesn't see how it's useful.

He admits that he might have missed out, though. He explored crypto in 2013 and 2015 when Bitcoin was $100-$200, and again in 2017, when it was $3k. He just wasn't able to convince himself that it was a smart investment.

I’m not looking for a thrill. In my personal investments, I’m trying to stick with something simple that works. I get my adrenaline somewhere else — my business.

Tamir's business is where he aims to get the highest return on investment.

Make your biggest bets in your business

While he plays it safe with his investments, he's all about taking risks in his business. In fact, he plans to make ‘bigger bets’ as he goes.

He's currently on the hunt for CRM apps that he can buy for around $40k. He believes there is an opportunity to turn CRM apps into enterprise products — you throw SOC2/GDPR compliance on them and they sell for 10x the price.

My partner and I joke that since 2020, I’ve been trying to run out of cash but haven’t been able to yet. I try not to stress too much about money. Instead, I spend as needed to move myself forward.

You can watch his bets unfold on LinkedIn. And check out Thank You GPT, ClearSight, and Adelante.

Please note that the above are opinions. This is meant for informational purposes only. It is not intended to be financial advice.

And if you'd like to be featured as a guest in a future interview for this series, let me know in the comments!