Stop Gambling with Your Business: Smart Financial Strategies for Entrepreneurs

Entrepreneurs are worse than gamblers…..

This week’s blog is all about Financial Strategies and Systems. Ever play the lottery? I have some news for you, you just hit the jackpot on your future success. Put on your darkest shades and your best poker face and place a bet on yourself. 


Welp, you either filed your t*xes by now or hopefully filed an extension on your t*xes… 



Right now is a great time to reflect on your financial business practices and set your 2025 up for success. Start with new tools, systems, habits, and practices to put into place so that you’re not freaking out each and every April. 



Also, if you aren’t freaking out each April, I’d love to know if you’re a lot like the women I’ve been interviewing for my graduate program. Time and time again I’ve heard these entrepreneurs say that they time block to help with their productivity. 

But, one quote in particular is one I’ll never forget, “Entrepreneurs are worse than gamblers.”

We were talking about her business and physical products, she laughed and used that quote in reference to purchasing inventory. She said she’s always trying to take $500 and at least double her money. I can’t lie, this totally hit home for me.

I would never consider myself a “gambler,” unless you count all the times I was ADAMANT that I was right when correcting my husband and would say “Oh yeah, I bet a (insert VERY expensive item.)” And, I’ve lost a time or two….thankfully we didn’t shake on it.  However, I’m not a sports gambler or into BlackJack or Poker, but you better believe I *will* bet on myself when it comes to business and entrepreneurship. And like the research participant I interviewed, I’m trying to double my money. 


I’m not an expert on gambling as I said, however, it is clear that we as entrepreneurial gamblers need a strategy. Which is why now is the time to set yourself up for 2025.  

I could pretend to write about how you could try “Gratitude Accounting” or “Treat your Financial Spreadsheets like a Zen Garden” and we would both know I’m full of sh*t. Here’s a fun lil fact for ya, a report by the U.S. Small Business Administration found that entrepreneurs spend an upwards of 120 hours per year on t*x prep - that’s three weeks. As entrepreneurs, we only have two resources: time and money. News Flash: Your t*x prep uses both!

Create Strategies……..


Some ways you can better leverage your resources are to create better financial strategies that can help you not stress out, burn out, or lose out on time and money.

  • Use Digital Tools: If you aren’t using software to help you categorize and track expenses, wake the f*ck up and move into the digital age girlfriend. I use Quickbooks, but have also looked into Freshbooks and Mint for future financial business tracking. 

  • Bookkeeping Weekly, Reconcile Monthly, & Audit Quarterly: Set aside one day per week to check in with your register. I prefer “Finance Fridays,” which is usually also when I run payroll. The best way to create habits is to stack them for success. By time-blocking each week you are better set up to keep your calendar and your budget, expenses, revenues, and hopefully profits on track.

  • Invest in Education: If you REALLY want to do your own t*xes, educate yourself. Take a course, watch a YouTube, or spend time understanding the financial tools you use to create more efficiency in your finances.  

  • Mindful Money Practices: While “Gratitude Accounting” is all fluff, there really is solid wisdom in approaching your finances with mindfulness. Do you really know your business numbers? Can you “Price is Right” guess your bills without looking? By understanding and acknowledging the intention of your expenses and appreciating your revenues, you can truly transform your relationship with money and financial decision-making.. 

  • Just Hire it: If all else fails and you hate everything that has to do with bookkeeping, t*xes, or financial statements, outsource that sh*t. Once again, all you have is time and money, why waste both? If you know that hiring it will help with your sanity, and your time, and ultimately make you a better business owner - you’re welcome, because your question was answered by you. Just hire a bookkeeper and be done with it. 

Ready for your reality inventory, it’s time….Ask yourself:

  • What worked when it comes to your business finances? - Think about your business practices, habits, and goals.

  • What didn’t work when it comes to your business finances? Think about your business practices, habits, and goals.

  • How are you sabotaging your business finances? - Think about your business practices, habits, and goals.

  • What is one change I can *actually* implement moving forward?

Want to get REAL accountable? Reply back to this email with the change you want to make and I’ll check back in with you to see how it’s going… “Oh sh*t…” I know! 

I’ll go first. My change: each week when I do my weekly bookkeeping, I’m also adding email receipt filing to the list. I’m actually really good about my weekly, monthly, and quarterly financial check-ins, however, I’m a spender (no shock there!) But, this year when it came to t*x time, it was a scramble going through all of my emails because I didn’t have my receipts better organized. a This change is small but necessary to not waste time. 

Lastly, I’m throwing you a bonus fact: according to a study published in the Journal of Applied Psychology, time blocking can increase your productivity by up to 150% - that doesn’t mean just more time for your business, but more time for you and your gambling. 


Stop gambling with your time and go back to doing what you love, being a professional gambler, AKA Entrepreneur. 

Remember, every minute spent scrambling during t*x season, is a resource taken away from innovating, networking, and growing your business. Invest your time wisely and reset your systems, habits, and practices for next year with a mindful approach that isn’t just fluff. 

If you’re daring enough to gamble on accountability don’t forget to send me your commitment for change. I’ll be here, cheering you on and sharing my own financial missteps, victories, and stories. 

Be courageous enough to bet on yourself, because you are capable of what’s next. Use your strength to propel you and your business forward, because your winning hand is coming up! 

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From Loopholes to Launchpads: Transforming Entrepreneurial Excuses into Stepping Stones