914: The 5 Business Mistakes I Learned the Hard Way (So You Don’t Have To)

The Goal Digger Podcast | Top Business and Marketing Podcast for Creatives, Entrepreneurs, and Women in Business

Jenna Kutcher | Entrepreneurship, Business Strategy & Marketing

Business, Marketing

4.8 • 12.3K Ratings

🗓️ 17 September 2025

⏱️ 32 minutes

🔗️ Recording | iTunes | RSS

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Summary

When I think about those first few years as an entrepreneur, I see a woman who was so full of fire and determination, but honestly had no idea what she was walking into. And I love her for that! Now, after years of growth, evolution, and yes, plenty of beautiful failures, I can see the patterns so clearly. The places where a little more strategy could've saved her months of spinning her wheels, where better boundaries could've prevented that inevitable crash, where more courage to be seen could've accelerated everything. This episode originally aired a while back, but I'm bringing it back because these lessons feel so relevant right now. Because here's what I've learned: we don't get to skip steps. Every fumble, every pivot, every moment of not having a clue was preparing us for what's next. And if sharing these lessons can help you honor your own journey while maybe sidestepping a few of the more painful detours? That feels like the most beautiful full-circle moment. So whether you're in your own 'figuring it out' era or you're revisiting this with fresh eyes, let's dive in with so much love for the versions of ourselves who were brave enough to begin! Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/ Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/ Goal Digger Show Notes: https://jennakutcherblog.com/different Thanks to our Goal Digger Sponsors: Sign up for your $1/month Shopify trial period at http://shopify.com/goaldigger. Find a co-host today at http://airbnb.com/host. Start your risk-free Greenlight trial today at http://greenlight.com/goaldigger! Spend $250 on your first campaign on LinkedIn Ads and get a free $250 credit for the next one—no strings attached. Just go to https://www.linkedin.com/goal. Shop SKIMS Fits Everybody collection at http://skims.com/goaldigger! Ready to see what powerful banking can do for your business? Visit http://www.mercury.com/goal to apply in minutes. Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC. The IO Card is issued by Patriot Bank, Member FDIC, pursuant to a license from Mastercard. Working capital loans provided by Mercury Lending, LLC NMLS ID: 2606284.

Transcript

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0:00.0	This episode is supported by What Should I Do With My Money from Morgan Stanley. This podcast makes
0:07.1	getting advice about your money less intimidating. I checked out the episode about early retirement
0:12.2	on what should I do with my money and honestly, I couldn't stop nodding along. It really got me
0:17.2	thinking about what financial freedom actually looks like, whether that's
0:20.9	being able to take time off without panicking, switching careers, or just having enough saved
0:25.6	that you're not constantly stressed about money.
0:28.3	The fear of never having enough while still wanting to actually enjoy life, I think we've
0:32.9	all been there.
0:34.1	Maybe you're wondering if you can ever get ahead or if building any kind of financial
0:38.4	cushion is even possible with everything else going on. What I loved was hearing about how you can
0:43.8	build flexibility into your finances with smart investing and planning no matter where you're
0:48.6	starting from. It made financial freedom feel less like some impossible dream and more like something
0:53.4	you can work towards step by step. Search for what should I do with my money in your podcast player and will
0:59.1	also include a link in the show notes. My thanks to what should I do with my money and Morgan
1:03.7	Stanley for their support. Can we talk about business regrets for a second? Because while everyone loves to say they did never
1:12.8	change anything, I'm over here thinking about five things I definitely would have done differently
1:17.9	in my first few years. The plot twist? I'm actually grateful for every single misstep.
1:24.6	I'm Jenna Coucher, and I help you trade hustle for purpose and build a business that gives you
1:30.2	the life you actually want to live. From a $300 Craigslist camera to a seven-figure business I run
1:36.6	from home, I've learned that success isn't just about what you do, it's about how you live.
1:43.2	Here, you'll get strategies that work, systems that give
1:46.7	you your time back, and steps that turn your effort into results and impact. If you're ready
	...

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