Thoughts on startup marketing, software, and technology

The Art of the Side Hustle: Pivot as Needed

Published May 24, 2017 - 0 Comments

Hopefully you have carved out time and the momentum is moving forward. With an active side hustle in the works and some real customers, you should start to understand what is working or not.

Pivoting is putting that knowledge to use towards adjusting the tools of your side hustle business.

You will find that some initial assumptions are confirmed, others not. Surprises will be had and that is to be expected. This is how pivoting is valuable. Admit where you miscalculated and adjust accordingly.

Keep your emotions out of it. The data should paint a clear picture and it may be painful to your ego. That is OK; we have all been there.

Much of what I have read about pivoting focuses on product market fit. This is vital, but is basic and obvious. I realize you understand the need to have something people want and ensure they know about it.

Pivoting your side hustle is about evaluating every process in your business engine. For example:


No matter how great you are nobody is buying if they do not know about you.

The Beatles, after playing just local gigs in Liverpool, ventured to play their first show in the London area.

This was to be their big breakout show and a huge crowd was expected. And then…

18 people showed up.

Their manager had failed to get the concert ad placed in the local newspaper before the show. So nobody knew about the Beatles gig that night. The manager was immediately fired to be replaced by Brian Epstein and the rest is history.

If The Beatles could not sell without effective marketing, do you think you can?

Ask yourself:

  • What is working with your marketing? What is not?
  • Is your price per acquisition sufficiently lower than your customer lifetime value? It better be or you will be running out of money soon.

One Million Dollars


At first our TribeBoost pricing was so ridiculously low that we were losing money on all clients.

Had I not adjusted this very early on, the business would have died years ago.

Pricing is a necessity to get right and get right early. Pricing may be the most important business feature that gets the least amount of study.

Many founders just pick a price out of thin air. At least I know I did. I just picked a price “that felt right” instead of one based on logic.

Big mistake.

Sadly a common entrepreneurial error is pricing too low. We are not confident at first that others appreciate our value.

At TribeBoost we increased prices four times thus far. Each time I expected to see a drop off of new sign ups.

That never happened.

Our new business always grew faster after a pricing bump. What I realize now is that our clients care more about quality, customer care, and integrity instead of a cheap solution.

Experience has also taught me that those that care about pricing first are not good clients. They don’t have a solid understanding of digital marketing, are not strategic thinkers, and are very needy.

They also don’t stay onboard very long — even after the extra help and attention we shower these clients with.

Buy Cheap, Buy Twice

You can price your offering so low it cripples perception.

Would you buy a diamond ring for $100? You would never trust it was real — even if it was.

With higher pricing we had an increase in enterprise and Fortune 500 clients. I worked at a few multi-billion dollar companies and we always picked the most expensive solution — as long as it was within budget. It felt safer. Going after some new or cheap solution was sticking your neck out and the most expensive is often assumed to be best.


I see entrepreneurs get overly obsessed with perfecting branding and identity too soon. It can eat up hours of time and swallow your budget.

While I understand the obsession and love branding and design myself, I think it best to brand in baby steps.

Wait until you have some cash flow and real clients first before spending serious money and time on this.

Focus in the beginning on product market fit and your marketing. You can tweak your branding later when you have established that the side hustle is growing and has a cost-effective marketing engine.

Then spend money on things such as:

  • A more refined logo
  • Better or more domain names
  • Branded podcasts
  • More effective web site design
  • Refine social media graphic design (avatars, header images, etc.)
  • Branded content marketing

Remember nobody is buying from you initially because of your great branding. They are buying because you are solving a problem they care about.

After some real interactions, it will be clearer what is resonating with your clients. Take that into account and tweak your branding accordingly.



Now that you have a real business with customers you are ready to reach out to those who can help.  Doing partner outreach too early may not work so well.

Who are you again?

I remember a scathing, “Why should I think you can grow my Twitter followers? You only have a few thousand Twitter followers of your own.”


This would be a smoother sale now that I have over 50,000 followers.

Build up some credibility and confidence to better approach more established organizations or influencers.

Don’t Be Self-Centered

A common mistake is asking someone you do not know to help you. Are you truly asking a busy and successful person (that you do not knowout of the blue to help you?

Meditate on the couch for a minute on how crazy and self-absorbed that is.

Why should they care about you? What normal person would? While this rarely works, it also just makes you look like a foolish amateur who needs more life experience.

A better way of reaching out to influencers is a brief introduction with an offer to help them out — and for free!

If you help, later on you are in position to ask for your own needs. Most good business people get it and spread the love around to you down the road without prompting anyways.

Here were some specific partnerships that were effective for us and may be for you too:

Sponsoring podcasts

Find a podcast in your niche that you can support. In exchange for support (money, free use of your product, referral or affiliate commissions, etc.) your business gets a mention on the podcast. I suggest using a coupon code or special URL to track referrals then pay a referral fee to the podcast.

Working with influencers

Find influencers who you believe you can assist. Help them by use of your product or whatever else you can do. Often this will result in referrals or good word of mouth.

Other businesses

Know a business that can help — and you can help in return? Contact them and work out arrangements. Don’t be shy, the least they can say is no.

Sometimes I get no response in these situations…complete crickets. Now I just learned that they are asleep at the wheel or simply arrogant. Both not good qualities and possibly helpful intel later.

Remember this pivoting phase of your new side hustle is very vital.

If you make smart and timely adjustments it will greatly increase your forward progress. I believe this phase is very much a make it or break it scenario for any side hustle hoping to turn into a real business.


* Here are the other articles in this series — The Art of the Side Hustle