2216: The Art of the Side Hustle: Overlapping Your Day Job with Entrepreneurship by Tex Freitag with Len Penzo on Starting A Business
Optimal Work DailyOctober 25, 2026
2216
00:07:31

2216: The Art of the Side Hustle: Overlapping Your Day Job with Entrepreneurship by Tex Freitag with Len Penzo on Starting A Business

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Episode 2216:

Tex Freitag explains how to overlap a day job with entrepreneurship by growing a side hustle into a full-time business. He covers building a savings cushion first, choosing a venture with a small entry point that draws on existing job skills, and reclaiming evenings and weekends through better time management. The takeaway is that a side hustle is the low-risk way to start a business, but only for those willing to sacrifice the free time it demands.

Read along with the original article(s) here: https://lenpenzo.com/blog/id49055-the-art-of-the-side-hustle-overlapping-your-day-job-with-entrepreneurship.html

Quotes to ponder:

"In almost all circumstances a side hustle shouldn't require large amounts of money to begin, and you should identify a small entry point which you can expand from."

"Every minute counts when you're working a job and running a business, so doing things like bulk cooking on the weekends can save you valuable hours each week."

"If you want to succeed and eventually transfer that side hustle into a full-time business, you need to make the sacrifices necessary to provide yourself more time and financial flexibility."

Optimal Work Daily is a daily career advice podcast where we narrate the best articles on productivity, entrepreneurship, and work-life balance, read to you by a professional narrator so you can grow your career a little more every day.

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[00:00:00] You're listening to a quick ad. You know what else is quick? Selling your car on Carvana. Just put in your vehicle information and we'll give you an offer. Done. No hassle, no negotiation, no guy from an online listing lowballing you. Which means by the time I'm done explaining this, you could have basically done it. Still haven't started? Hey, better late than never. Sell your car today on Carvana. Pickup fees may apply.

[00:00:29] UKG is the workforce operating platform with unified HR, payroll and workforce management. Built to solve the unique challenges of frontline work. Powered by People First AI and decades of labor data, UKG turns workforce intelligence into real-time decisions around staffing, pay, compliance and productivity. Enabling every worker to confidently take action as work happens. Because when work works, everything works. Learn more at ukg.com slash work. UKG, HR, pay and workforce management.

[00:01:00] This is Optimal Work Daily. The Art of the Side Hustle. Overlapping your day job with entrepreneurship. By Tex Freytag with LenPenzo.com. Very few businesses today are started by those without existing careers. Instead, many choose to take a well-paid job and then create another business in their spare time, only to go full-time when they're confident. In principle, the side hustle provides a low-risk, creative, money-making outlet that can be used for a long-time job.

[00:01:29] It allows a graceful transition into becoming a full-time business owner. However, the reality is sometimes harder. A side hustle is, by nature, going to eat away at your free time. Therefore, you must be dedicated and passionate, as well as equipped with the right tactics to overlap from your current job to entrepreneurship. Number one, saving money from your job. Even the leanest of startups are likely to require some capital. And if not, they'll demand large amounts of your time before they generate revenue.

[00:01:59] In this case, it's wise to have as much personal savings as possible so that you have a safety cushion and so that you can continue to work on your business even without any income from your job or the company. Although it can be wise to keep some of this money in a checking account so that it can be easily used by your business, an investment account will generate greater returns. Choosing between two of the most common options, variable annuities versus taxable mutual funds, can be tough, and the right choice depends upon your financial situation.

[00:02:28] Regardless, both offer far greater returns than the interest from a checking account. Saving in this way will give you a financial buffer that you'll need to either invest in your company or to use for your costs during the transition from a job to entrepreneurship. Two, identifying the right side hustle. Some companies, by definition, will require large amounts of time even from the beginning, and these are unlikely to make a great side hustle. Instead, you want to identify a business which can be started as a side hustle

[00:02:57] and then eventually scaled into a full-time company that can generate you millions of dollars in revenue each year. Often, you might have a skill or talent that you can use as an entrepreneur. For example, if you're employed as a mortgage advisor, you might more easily be able to start a company that buys and rents out condos or homes. Regardless of your job, you'll have some skills that can be transferred into a business, and as long as that business is something that interests you, it could make for a brilliant side hustle that eventually can be a large company.

[00:03:25] While it pays to think long-term and to consider the future, you must also ensure that it's possible to do as a side hustle in the evenings and weekends. In almost all circumstances, a side hustle shouldn't require large amounts of money to begin, and you should identify a small entry point which you can expand from. For instance, if you're a cleaner, you might decide to start freelance cleaning, then hire cleaners to work for you, and eventually buy shabby houses and clean them up for resale.

[00:03:52] Do you see how you can go from a small entry point into a potentially tremendous business opportunity? While you're not restricted to businesses that use your existing skills, it can make the transition far more accessible, and it prevents you from having to learn on the job. And three, managing your time effectively. The most difficult part about a side hustle is that the time you have to work on your business will be the time slots that you want to use for relaxing with your friends and family. The weekends and evenings are no longer yours.

[00:04:22] They are the businesses. And to overcome this and still have an enjoyable life, you need to learn to manage your time effectively. If your current employer is willing, you might consider adjusting your work schedule so that it fits better with your new lifestyle. For many, this could mean working from home where possible, starting earlier, and leaving the office at 3 p.m. instead of 5 p.m., reducing your commute at both ends. Similarly, once you get home, it's important to make a conscious effort to sit at your desk rather than on the couch,

[00:04:52] working on your side hustle before relaxing for the evening. Every minute counts when you're working a job and running a business. So doing things like bulk cooking on the weekends can save you valuable hours each week. The side hustle has become immensely attractive in recent years, but it can be incredibly challenging. If you want to succeed and eventually transfer that side hustle into a full-time business, you need to make the sacrifices necessary to provide yourself more time and financial flexibility.

[00:05:23] You just listened to the post titled, The Art of the Side Hustle, Overlapping Your Day Job with Entrepreneurship, by Tex Freytag with LenPenzo.com. Observe. Observe. The North American dad. 50s. Great polo collection. He enters his vehicle information on Carvana. An offer appears in minutes. Remarkable. He squints, reads it again, smiles and says, Dang, that's a good offer. The highest form of approval.

[00:05:52] No haggling. No hassle. No one called him boss. He's still on the couch. Astonishing. Sell your car today on Carvana.com. Pickup fees may apply. UKG is the workforce operating platform with unified HR, payroll and workforce management. Built to solve the unique challenges of frontline work. Powered by people first AI and decades of labor data, UKG turns workforce intelligence into real-time decisions around staffing, pay, compliance and productivity.

[00:06:20] Enabling every worker to confidently take action as work happens. Because when work works, everything works. Learn more at UKG.com slash work. UKG. HR, pay and workforce management. And thanks a lot to Tex for this post, which he of course wrote for Len Penzo's site. And let me tell you a little bit more about Len. Len Penzo writes about personal finance and macroeconomics on his eponymous Personal Finance blog, which has been twice honored as a Kiplinger Best Money blog,

[00:06:49] and honored with two Plutus Awards for Best Personal Finance blog. Len's personal finance articles have been featured in the New York Times, MSN, Business Insider, Money, Time, Forbes, The Huffington Post, Yahoo Finance, CBS Money Watch, and Clark Howard, just to name a few. Len's focus is on the importance of personal responsibility, not only for our personal finances, but also for everything else we do in life. For more from Len, you can come by lenpenzo.com.

[00:07:17] That's L-E-N-P-E-N-Z-O dot com. That is going to do it for today. I thank you so much for joining me as always, and be sure to tune back in tomorrow for another article, and that is where your optimal life awaits.