124: What I’ve Learned and Applied from 50 Awesome Entrepreneurs – Part Two

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At the end of nearly every episode of The Side Hustle Show, I ask my guests for their #1 tip for Side Hustle Nation. There’s always a great variety of responses, and I wanted to take some time today to go through some of my favorites from the past 50 interviews.

(I first did this for episode 50, which was my first-ever solo podcast recording.)

Through the first 50 episodes, there were a few common themes that stood out:

  1. “Just do it.”
  2. Adopt the “lean startup” mentality.
  3. Build your team / network.

If all these really smart and successful people keep saying these episode after episode as their “#1 tip,” I think they’re worth paying attention to.

What action can you take today to apply those tips?

My #1 Tip? Find your WHY.

Why side hustle? What are you trying to build? What will that afford you?

In this week’s show I dive into a meta analysis of the #1 tips from my next 50 guests. A similar pattern emerges with some variation of “just get started” remaining the most popular response.

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another 50 awesome entrepreneurs

Here are the tips. The ones in bold are the ones I spend some time talking about and applying in my work.

51. Alex Genadinik – 80/20 your efforts. 

52. Nick Reese – Give yourself artistic freedom and write daily.

53. Cameron Rambert – Make up in volume what you lack in (perceived) competence.

54. Kimberly Palmer – Just get started.

55. Chandler Bolt – Complete the process instead of perfecting the product.

56. Kimanzi Constable – It’s a marathon, not a sprint. Be you, be original, and don’t try to copy the A-listers.

57. Grant Baldwin – You can do this!

60. Jon Acuff – Don’t be ashamed of fear. “Average is living a life less than you’re capable of.” 

61. Ryan Grant – Get your mind right. Think, “How can I make this happen?”

62. Jesse Krieger – Take action and take it one step at a time. 

64. Scott Britton – Find other people with your same mission. 

65. Corrina Gordon-Barnes – Be alert to overwhelm, and understand overwhelm is a choice.

66. Josh Elledge – Don’t put this off!

67. Garrett Moon – Validate your idea.

69. Doug Cunnington – Do it today.

71. Kurt Elster – Solve simple problems.

72. Ryan Finlay – The best opportunities are found only once you’re already in motion. 

73. Matt Giovanisci – Spend 90% of your time creating and 10% marketing.

74. Harry Campbell – Think outside the box and don’t be afraid to try something out.

76. Alexis Grant – Be persistent. Stick with it!

77. Kellie Gimenez – Find something you’re passionate about and find a way to make money doing it.

78. Carrie Smith – You are your most important asset, so put yourself first and invest in yourself. 

79. J. Massey – Once you get started, stay started. Focus on your IGAs; your income generating activities. 

80. Jasper Ribbers – If you’re going to make assumptions, you might as well make empowering assumptions. 

81. Rob Cubbon – Be consistent. Keep the products coming.

83. Jessica Lawlor – Wake up earlier and start each day with your most important task.

84. Andy Slamans – Take action. Don’t be a career “learner.”

85. Scott Oldford – Don’t be afraid of failure.

86. Joshua Jordison – All business is done through people. Give them value first.

87. Bryan Harris – Get extremely specific. Read the book Built to Sell.

89. Nick Stephenson – Focus on building your email list.

90. Jon Nastor – Get started today.

92. Sean Marshall – Ask yourself what your values are, what you REALLY want, and what you can create. How do those align with a paying market?

93. Dayne Shuda – Think how BIG could this be 5-10 years from now?

94. Joshua Sheats – Find your actual net profit from your job. It might be less than you think. 

98. John Corcoran – Create a “conversations list” of 50 people you’d like to build a relationship with over the next 12 months.

99. Nate Dallas – Be honest with you are and be courageous. Do what you’ve been designed to do. Don’t shortchange yourself.

102. Dan Faggella – Build your list!

104. Will Mitchell – Think big, act small.

105. Jeremy Jacobson – Start today. Compound interest is the most powerful force in the universe. 

106. Dorie Clark – Dive in on content creation.

108. Mark Podolsky – Read The 12 Week Year.

110. Steph Halligan – Try something radically different.

111. Daniel DiPiazza – The less I have to do, the more I get done. 

113. Lise Cartwright – Done is better than perfect.

114. Melinda Fleming – Do the thing people notice you for.

115. Ankur Nagpal – Just do it.

116. Travis Marziani – Write down 1 idea a day. 

117. Justin Cooke – Find your ONE thing.

121. Tim Johnson – Make your value proposition obvious.

122. Natalie Sisson – Do or do not; there is no try.

OK that might actually be 51 by my count, but either way tons of great advice from Side Hustle Show guests.

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Remember, leave YOUR #1 tip below for a chance to win a free Side Hustle Strategy session!

UPDATE: Congrats to Ben from UCareerStrategy.com for winning the contest!

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

36 thoughts on “124: What I’ve Learned and Applied from 50 Awesome Entrepreneurs – Part Two”

  1. Thank you for the insightful post. I am going to bookmark this post, and share it with some friends. I thought that the details per person were going to be a lot longer, but having one sentence is much more efficient. I think that consistency is critical.

  2. As per the eps.
    Mine would be: Set Realistic Goals
    I have a small $20 tack board and I put my current jobs incoming per day and my side hustle goal income of just $25/per week. The other day I just realized I have surpassed my goal a longtime ago with just my Fiverr account (that now makes roughly $250 in income per month.) The thing is seeing those totals on that board gives my brain something to work on and I see it as soon as I wake up. It’s silly but having that works as an extra push when I feel down.


  3. Thanks for this wrap-up, Nick. My #1 tip: The night before, write a list of three things that must be done the next day. This allows for a restful sleep without anxiety, and a feeling of accomplishment as you cross them off your list!

  4. My number one tip:

    Don’t be afraid to stop doing something that isn’t working.

    It’s “sunk effort” – just because you’ve put a lot of effort into doing something previously, that shouldn’t necessarily influence whether you keep going in the future if it’s not working for you. Find something else.

    I did this recently with an online course I was creating. It didn’t “fail” necessarily (I never published it!) but I just realised it wasn’t aligned with what I wanted my side hustle to be. It was a hard decision because I spent a fair bit of time on it…


    • That’s an excellent one, Ben! In personal finance we talk about sunk costs in the same way (once you’ve spent the money it’s spent, even if you decide not to do the thing, so don’t throw more time/effort/money in just because you already spent some.) But I hadn’t thought about it in terms of suck effort in the business. Thanks! That’ll be really helpful!

  5. My number one tip is to leverage law schools in your area or your alma mater for free legal advising. There are numerous schools that offer a law student operated “entrepreneur clinic” that screens and takes on clients for FREE. Two that I know off the top of my head are the University of Michigan and University of Colorado (Boulder). Every program has eligibility requirements, but you’re missing out if you’re not looking into it. It’s a win win win!

  6. My #1 Tip is something I heard from a guest on the Hack the Entrepreneur podcast:

    “Money is made in turning the wheel, not re-inventing it.”

  7. I have several tips… so i will post one I haven’t seen in the comments as yet.

    Remember that our prospects & clients’ basic human state is that they want the *situation* to change (in debt, overweight, hate our jobs!)… while very reluctant to make a change or even try something new.

  8. A very amazing round up Nick, i really enjoyed all the quotes and also agreed to all of them especially the idea of waking up early and doing your most important tasks.

    Being an entrepreneur is never an easy task and we need these kind of quotes from people that are already walking the walk to keep us motivated from time to time.

    I’ve really learnt a bunch of things here and will keep them in mind, will even print out the page :).

    Thanks for sharing.

  9. I feel like I’ve been studying and hustling for 10 years and making no progress. Recently on your Pod Cast I learned two things: 1) Do the thing that you love because you love it, if you don’t love it you’ll never become profitable and 2) It’s hard for everyone. It’s lonely for everyone. That doesn’t mean you should give up!

    On this journey I’ve had people laugh in my face while I was describing my goals. I’ve faced many disheartening conversations with “only excuses” people, like you mentioned in this. What I’ve truly gained from you is the knowledge that all of this striving isn’t just being done by me. I’ve pushed myself to learn many things about business and success. I’m smart. I work hard. I can do this. I’ve recently refocused my efforts to pour my heart into building something that I love to do- even when no one knows I’m doing it. I hope it takes me where I want to go, but the road ahead seems long. Thank you so much for giving me a few minutes every week where I don’t feel alone in this struggle. You’re a true gift.

  10. I started listening to your terrific podcast about two weeks ago.

    The current episode is filled with great tips, but the most impactful for me is something I took from the episode with Dane and Wellington. Specifically, the idea of developing a mindset where you embrace empowering thoughts and dismiss the negative ones immediately.

    Thanks for putting this into the world, Nick!

  11. As the host of the Online Learning podcast and a committed life long learned, my tip won’t surprise you. Learn something new everyday and then make a three minute video sharing or teaching this knowledge and upload it to YouTube and elsewhere. Eventually, make a course from the content!
    Love the podcast. Thanks Nick! Best regards. John

  12. Loved this episode. The in-depth episodes are great, but these kinds of episodes every now and then are awesome. They’re like pep talks for your day!

    My best #1 tip comes from a local businessman I heard speak at conference last year (and have also connected with since then on a personal level):
    “Failure is okay if you fail fast and fail forward.”

    I like the idea of taking a leap and not being afraid of failure. And I was inspired of this idea of failure being an active verb that you can, in some ways, control (even if you can’t always control the fact that an idea becomes a failure). I like the wisdom of limiting your losses and improving.

  13. After years (yes, years) of “research” and “getting started soon” on my path as an entrepreneur I would say my #1 tip would be:

    Pick something. Anything! Anything that you think is a good idea, and give it a go. The only way to know if it will work or not, is to try it out! If it works, great. If not, try again with a new idea.

    I’m just recently starting to take this advice, after worrying I was becoming one of the many ‘career learners’ that would never take action.

  14. My number one tip is to reach out and make contact. My side hustle is a service based business. I was only moderately successful when I reached out offering a service. When I started reaching out more personally via statements like I love what you did with xxx or I am really interested in how you accomplished yyy I get many more conversations going and have ultimately landed more clients.

  15. To increase your rate of success, double your rate of failure.

    I got this from the ‘Slight Edge’ book.

    If your not failing quickly, then your not learning quickly.

  16. My tips isn’t original, but it has definitely served me well in the two and a half years since I became a dog sitter (and has, I believe, been one of the reasons I have doubled my humble income every year). My tip? Do more than people expect of you, and choose a job where you just can’t help it.

    I love dogs. They are my people. So I didn’t think twice when a client’s sweet old lab was being finicky about eating… and I started hand feeding him. Did I mention there was slimy canned pumpkin in the food? His people had been doing the same, but they didn’t think they could ask that of me. They now know that I love him as much as they do, and it makes them want to have me back again and again.

  17. I just came across KanbanFlow I use it to collect all the things I “Want” to do for my podcast, then move out the ones I need to do Today, then move them to “In Progress” then to “Done.” The mobile web version syncs perfectly with the web app (a la workflowy). Love your show Nick, and i’ll be adding “Leave Side Hustle Show Review” to my KanbanFlow :) cheers

  18. My number one tip:
    If you have a to do list or list of items for the side hustle, break it down to 30min tasks. It’s perfect for trying to get things done but you don’t have two hours each day. Before work, before dinner, after dinner, free second between meetings…. I found the key is to have a physical item you write on: post it note, journal…. It feels great marking something off and not feeling overwhelmed with everything to do.

  19. Hi Nick,
    I really enjoy your podcast!.
    My #1 tip is to join a mastermind group because “no one is an island” to paraphrase John Donne. It’s crucial to be accountable to a like-minded group of people who give open and honest feedback in a non-threatening environment. I found my mastermind group via your Facebook group. Thank you.

  20. Hi Nick,
    I love your podcasts – they are so informative and motivating!!

    My tip – know when your “genius time” is and maximize that time to focus on thinking/strategy/planning activities that will propel you forward.
    i.e. my genius time starts about 2 hours after I wake for 2-3 hours so I book specific activities in the calendar at this time (which do not include administrative tasks that take little “think” effort and can be done at other times of the day).

  21. Nick, this was fantastic. I listened on my long cardio day and I totally forgot about the boiling lava hot sun beating down on me or my behind cramping from all of the hills. Haha! I love and agree with Jon Acuff’s take on the consequence of living an average life, and of course the quote you shared, “If you don’t take care of your body, where will you live?” Thanks for keeping me company today!


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