100 Lessons We’ve Learned in Entrepreneurship

Apple Podcasts | Spotify

It’s hard to believe we are 100 episodes in, yet we still feel like we have just scratched the surface and have so much more to share! When we started this podcasting journey we weren’t sure what to expect. In fact, in the early days, we were actually at an event where a marketing expert actually said out loud “Podcasting is dead”. 😬

We wondered if people would tune in… and it turns out, you did. Since we started, we have over 30,000 downloads! We cannot thank you enough for listening to us, Instagram messaging us about how much you love the show, inquiring about working with us from the show, and telling your friends to listen, too. We are seriously so humbled by every single message we get. 

How lucky are we to be able to be in your ears? We promise to never take that for granted! And we hope to continue to bring you the absolute best, actionable, and authentic content we can. But you, my friend, are the real MVP. You are what makes this podcast continue every week. 

For today’s episode, Courtney had a crazy idea… “How about we share 100 lessons we’ve learned in entrepreneurship?” We’re always up for a challenge any day of the week. So here we go…. Rapid fire style.

Quick note: Some of these are lessons, and some are confessions— just keeping it real with you guys. 

1. Podcasting has been the easiest, most fun platform to create content on (definitely not dead).
2. Do the damn thing and quit your 9-5 and chase that dream.
3. There is no such thing as work-life balance.
4. Trying something new in your small biz and failing is okay. Been there, done that.
5. Running a business is impossible without help.
6. Done is better than perfect (says the perfectionist in us 🤪).
7. We are actually more productive on the days when we take a break to workout than the days when we power through working.
8. A beautiful Instagram grid is our weakness 🫠 even though we know the content we create is more important than how it looks.
9. It’s impossible to work with a 3- and 4-year-old.
10. Navigating loss and fertility issues while running your own biz is extremely hard — I (Court) am thankful every day for Abbey and her strength to keep me moving forward ❤️
11. Instagram feels so much easier to manage and take a break from now that we’ve taken the time to grow our audience consistently and authentically over the past few years.
12. Four years into our biz, and we still have absolutely no work routines. It’s our goal to be more organized next year.
13. The number of website inquiries coming in doesn’t matter — one week will be slow, and we will feel nervous, and then the next week, we feel like we can’t keep up.
14. Work when you feel most motivated, whether that’s at 5 am or midnight. You’re the boss now, and set hours are a thing of the past.
15. You definitely can read too many business and self-help books.
16. Protect your personal time. It’s so easy to go all in on your business and forget you have a personal life, too.
17. Investing in our finances early with Val was one of the best business long-term decisions we’ve ever made.
18. We had always loved the saying “Do what you love, and you’ll never work a day in your life” but we call bullshit on that now 🤣 We love what we do, but some days it is A LOT of work.
19. Asana is our security blanket for managing projects and to-do’s and if anything happened to this tool, we would definitely cry.
20. Burnout can happen even in your small biz. Recognize it and pivot to avoid it.
21. Showing up on video is easier the more often you do it.
22. Take time to celebrate your wins, big and small. We’re not great at this, and we’ve had a lot to celebrate over the years. That’s another goal of ours in ‘24.
23. I (Abbey) am thankful every day for the fact that I decided to run this business with Courtney 😘
24. Aweee right back atcha, friend. I (Court) absolutely could not and would not do this without you. Running a biz solo sounds so damn hard.
25. Healthcare wasn’t actually that hard to figure out, yet it feels like the scariest reason to leave a 9-5.
26. If you can, give back. Donate your goods or services to one or two clients a year. This is something we started doing this year, and we absolutely love it.
27. Google Search Console is a tool you absolutely need to conquer your SEO.
28. If you have a product or service you hate, ditch it. It’s not worth putting energy towards if it gives you nothing in return.
29. If you want to try something new— a course, a shop, a podcast— just do it. Better to have tried and learned than regret never trying later.
30. Batch your content— record reels, write captions, record podcasts, etc. Do it together and block your calendar. The efficiency in staying with one thing is key.
31. Being a good affiliate for your fellow business friends, tools, and systems is a lot of work if you want to do it well… but an amazing source of revenue.
32. Branding is so much more than just your logo. It’s everything you do for and in your business. YOU are your brand. Invest in it. It’s worth it.
33. Every business should use Profit First. Period.
34. We hated Voxer at first but now secretly love it. Our husbands, however, feel much different 🤣
35. Hiring a copywriter is worth every penny. That shit is hard.
36. Crying in or about your business is okay. It means you’re passionate and that you work really hard to make that shit run daily.
37. You don’t need Instagram to be successful, but you do need Google (you might not agree, but that’s our opinion!)
38. Family is more important than anything else. Period.
39. When imposter syndrome hits, shut down all social media.
40. Hire out the things in your biz that bring you absolutely no joy. You don’t have to love it all, and you certainly don’t have to do it all either.
41. We are in marketing. We aren’t saving lives. Whatever it is can always wait until tomorrow.
42. I (Court) have a love-hate relationship with Canva. My guess is most professional designers do.
43. Email templates are a crucial time saver.
44. Being ghosted is quite literally *the worst*. Try not to be that person.
45. Whether I (Abbey) am using Semrush or Ubersuggest to capture my clients’ SEO research, I have still seen incredible results. You don’t need an expensive tool to see SEO growth.
46. ShowIt is the easiest website platform we’ve worked on to date, and will always highly recommend it. Wix is the hardest and most painful when it comes to being creative.
47. Hiring a bookkeeper is another favorite investment — shout out to Madison Dearly and her team who might just know our books better than we do.
48. Naming a business is hard. Be smart about it and hire that shit out. Also, be sure to check for a domain AND that it’s not trademarked by someone else. Also, spelling…
49. We should have been more prepared when we were on Jenna Kutcher’s Goal Digger Podcast.
50. Giggling about #49 🤣 We should be prepared for a lot more things in our biz, but here we are #thriving.
51. Running an agency and doing all the marketing things is not for us— branding and SEO are our sweet spots.
52. Show up authentically. People can see right through you if you don’t. We truly believe this is a huge part of our success.
53. Always let your potential clients lead the discovery call. They should talk first. Then, be sure to actually listen and speak to how your offerings will solve their problems.
54. We definitely don’t think the client is ALWAYS right. Put on your professional hat and explain to clients why you think your (fill in the blank) might be better for them and why. If they still disagree, you did your best and tried.
55. Failure = content.
56. Working with our babies on our hips is our favorite, even if it is chaotic some days. We absolutely will not change that for anyone or anything.
57. You don’t have to accommodate someone else’s schedule, even as a service provider. You are in the driver’s seat of your time.
58. Remember to eat your lunch 🤪 
59. Working outside the home is necessary sometimes.
60. Cheap blue light glasses suck, spend the money on a good brand like Felix Gray and stop shopping on Amazon.
61. Stop selling the details and start selling the solution… meaning don’t tell me the features and benefits of your product. Tell me how this product is going to change my life.
62. Repurpose, repurpose, repurpose.
63. Learning our enneagrams has helped us understand what drives us and why.
64. Shut down your email for a day if you need to get shit done. It’s so easy to constantly “check in” but that does you no good when it halts your productivity.
65. Being a guest on other podcasts is a great way to drive business.
66. You don’t need 20 hours open on your calendar for discovery calls. It’s okay that people are booking out a few weeks when your calendar is full. 
67. Zoom is not great for recording guest podcasts.
68. Fresh air is good for the brain and body.
69. Always pay for the annual plans, not monthly.
70. Don’t push it on your off days. Some days you crush it, and others you just exist 🤣
71. We have officially hit the point of needing a proper payroll system.
72. If you have a biz bestie like we do, compliment them on their good work, remind them they’re doing great, and tell them to log off and go for a walk. The littlest bit of acknowledgment and encouragement goes a long way.
73. Being a person who takes feedback and criticism with stride is rare and so dang valuable.
74. Brand photoshoots are a must.
75. We are recovering people pleasers learning when to stand our ground and how to value our worth.
76. The comparison game is real. We compare ourselves to brands we want to look or be like all the time. However, the longer we are in our biz, the less we do this. WE are the brand, and people love us for who we are. Be true to yourself, and remember that your followers and/or clients choose you for YOU.
77. Everyone else is too worried about their own grass to care if yours is green.
78. It’s okay to be steady or calm in your business. There’s no need to be creating something new ALL of the time. Just being consistent and coasting is completely okay. 
79. Prioritizing travel, community, and events is key to growing.
80. Automation in your biz is a must. Trust us.
81. Leads and connections can come from anywhere (old colleagues, friends of friends, neighbors, etc.)
82. Stop using 30 hashtags 🤣 Instagram doesn’t care, and neither does anyone else.
83. Having uncomfortable conversations as business partners is the only way you will survive together.
84. You don’t have to meet with your client at every touchpoint of a project. Video walkthroughs have been a lifesaver for us. 
85. Transparency… the less we hold back, the more vulnerable we are, and the more we actually connect with our audience.
86. You absolutely can (and should) say no to clients who don’t fit with you or your business. If it’s not a good match to start, it won’t be a good match later.
87. Don’t buy the cheapest tripods on Amazon (btw, if you have a tripod or ring light you love, send it our way!)
88.  I believe having your favorite beverage while you work keeps you motivated, sane, and happy. Coffee, water, and sometimes wine are our bevies of choice. Coffee is a must, though!
89. Spend less time watching other people run their business and more time running your own.
90. Take vacations! It may seem like vacationing is easier because you are your own boss and you make the rules, BUT because you are your own boss and invested in your biz all of the time, vacation often gets overlooked, and then never happens. 
91. There is always a next goal, but don’t forget to celebrate the now goals.
92. Start planning your holiday party in September— put it on your calendar now. 
93. The entrepreneurship community is the absolute best cheerleader.
94. Anyone can start and sell anything. But it’s the people who take action that will be successful. 
95. Focus on building wealth, not money.
96. Be silly more often. Stop trying to look perfect.
97. It’s not our VA’s job to bring in sales— it’s ours.
98. We are ready to go deep, not wide, in our offerings. 
99. Taxes are hard. Hire someone you can trust.
100. Even though we are 100 episodes into podcasting and 4 years into our business, we feel like we’ve just scratched the surface. 

Again, thank you for joining us on our podcasting journey. We can think of more than 100 lessons we’ve learned in entrepreneurship, but these are the foundations of where we are today. Thank you for supporting us, and Happy New Year!

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Abbey Oslin and Courtney Petersen are Minnesota-based marketing experts, educators, and co-founders of boutique marketing agency Duo Collective, which specializes in SEO, social media strategy, and branding for small business owners and creative entrepreneurs. To learn more about Duo Collective or to inquire about working with our team, head over to www.duocollective.com. 

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