119: Side Hustle Coaching: What it REALLY Takes to Build a SaaS Business, with Special Guest Dane Maxwell

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It’s been almost 2 months since we last caught up with Wellington, one of my public coaching volunteers. Where we left off, he was working on a smartphone app for travel hackers and kicking around the idea for a software business in the home renovation estimating world.

Our last session was a rough one.

Wellington had just broken his foot and had his app repeatedly rejected from the app store for bugs that needed to be fixed. To make matters worse, his day job had become increasingly demanding and he was putting in 60-70 hour weeks at work.

The good news is that while the day job workload is still pretty intense, the foot is healed and the app was approved! He’s even earned $1.65 in advertising revenue and in-app purchases for the Pro version.

That’s a great win where I feel like we really needed one.

It’s obviously not a ton of money, but remember Wellington made $0.07 online last year, so he’s pretty pumped about it. In the next few weeks we’ll revisit the app and figure out how to market it to try and bring more users on board.

But in this episode, we’re focusing on his software as a service idea — with a very special guest, Dane Maxwell from TheFoundation.com.

We’ve referenced The Foundation as we’ve discussed the idea and next steps during past conversations, and I thought it would be awesome to invite Dane on to provide some expert one-on-one guidance.

(The Foundation is a premium entrepreneurial education program specializing in exactly the type of software business we’re talking about.)

Graciously Dane agreed and we were able to record this session that’s honestly unlike any other episode of The Side Hustle Show. It gets a little raw, a little emotional, a little vulnerable, and maybe even a little awkward at times, but I think we come out the other side a little clearer and a lot more empowered.

I left the audio relatively untouched, which means there are some longer-than-usual silences. Don’t worry, it’s still playing. Use those times to put yourself in Wellington’s shoes and see how you would answer the question.

Let me know what you think in the comments below!

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  • The easiest way to test if your mindset in the right place. (Do you have or are you getting the results you want?)
  • The two questions to ask when faced with fears and doubts.
  • Why a 6-figure business doesn’t require THAT many customers.
  • The one biggest pain point Wellington has extracted so far.
  • Dane’s suggestions for email outreach, product prototyping, and pre-sales.
  • What it means to “marry their problem” and why that single ability separates decent entrepreneurs from truly great ones.
  • The 10% Price-to-Value Rule.


Potential Outreach Scripts:

Version 1:

“Hey would like a tool that lets you quickly estimate prices so that your bids are accepted on the first day? 

P.S. No I don’t have anything to sell you — just curious if that’s something you’d want.”

Version 2:

“I know how hard it is to find work, and I know how hard it is to keep work, let alone take care of your team. I’m a fellow contractor and am wondering if we might be able to brainstorm and maybe make our businesses better together. Would you ever be open to having a discussion with me?”

(Then during the call, let them know about your product development intentions.)

What do you think? If you have any feedback for Wellington (or me) based on this call, be sure to let us know in the comments below.

saas business

21 thoughts on “119: Side Hustle Coaching: What it REALLY Takes to Build a SaaS Business, with Special Guest Dane Maxwell”

  1. I have been listening to your podcasts for the last month and I have to say that this is by far the absolute best podcast I have ever heard in my entire time of podcast listening. Extremely inspirational for all of us waiting and too insecure to make that jump. I would love to hear more podcasts like this!

  2. As a .Net Developer for 10+ years with a couple Saas Apps under my belt I have to say owning my own ‘successful’ SaaS is very fascinating. I have heard Dane Maxwell and listened to many interviews with him and his students. As with most interviews (with Dane and on SideHustleHation) this is a good one. I would love an opportunity to take Dane’s course.

    Spontaneous thought, If anyone is considering a SaaS I would enjoy having someone to talk to about this kind of stuff or to bounce ideas off of.

  3. This Dane Maxwell episode was freaking amazing.

    It was weird at times with the deep breathing exercises etc, but it really brought out some things from Wellington that really resonated with me.

    Keep it up Nick (and Wellington). Loving the podcast.


  4. Nick, Dane & Wellington,

    An incredibly powerful episode guys and Nick… fantastic decision to leave the editing to a minimum. Very effective and made the episode quite riveting for myself.

    Wellington ~ looking forward to following your next steps. Positive vibes being sent your way from up here in Canada.

    Nick ~ Great job as always… Always look forward to listening to Side Hustle Nation each week.

  5. That was great. The hippy stuff doesn’t bother me and anyone who can’t see the value of Dane’s approach is deluded. I loved the bit where he asked Wellington to get less fierce.

    I’m totally checking out The Foundation now.

  6. Nick,

    I enjoyed the podcast though it did get a little out there. I wonder if Dane has ever told someone while doing this exercise that they’re not cut out for entrepreneurship.

    I was probably projecting my own thoughts about the outcome of this public coaching, but to me, it seemed Wellington was answering Dane’s questions with what he thought Dane wanted to hear instead of what he was actual thinking. Dane had a few “These aren’t the droid you’re looking for” moments that seemed to pull Wellington into certain answers.

    I’m pulling for him though. I hope it works out in the end.

    • Great point – I remember thinking that too…”Is Dane going to tell Wellington that he doesn’t want it enough and he’s not cut out for this?”.

      Scary thoughts to face up to for a side hustler…


    • Yeah specifically the part about imagine caring soooo deeply for this contractor you’ve never met. I’d definitely have a hard time answering that w/ “yes.”

      I think the biggest challenge is just the lack of time so we’ll work on some time hacks to see if we can get this initial outreach and research done effectively.

  7. What a great episode. Was raw and inspirational. As someone standing on the sidelines of getting a side hustle, this episode really resonated with me.

  8. I’ve been listening to your podcast for about a month now and the direction this episode took (thanks to Dane’s questions) was excellent! I was on the fence, but now I’m committed.

    Other episodes provide great insights coming from success stories in specific fields/ventures, but the specificity can be limiting for me. Wellington’s side hustle may be a specific audience, with a specific product; however, Dane’s advice and guiding questions provide a benefit to ALL side hustles.

    We’ll played sir, well played.

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