HMBT #142: Lessons From an Entrepreneur

Today I am joined by Kirk Deis from The Bug Squasher and Treehouse 51. Kirk, came on to the show to share some lessons he learned while starting up and running two businesses.

I am recording this episode while I am in France and Kirk is in Newport Beach, California. We are both dealing with the heat in different ways.

Kirk mentions a line from Matt, a person on his team; “How do you know what you don’t know?” You will not know it until you are in that situation. Kirk started an agency, Treehouse 51 and learned that running a business is not easy. He says that there are so many things to think about when you are not working a 9-5 job.

It is important to learn from other people’s mistakes. Kirk talks about a lesson he learned when he brought on a new client when they were hungry for work. They did work for a client and they liked it. When he sent the invoice, the client wanted to work with them more. At least that is what he thought. They ended up going silent and not paying the last invoice.

Be careful of “dangling carrots”, or the promise of ongoing work. The lesson is that when you work for a client, have a contract and credit card on file. You need to protect yourself, even when you are hungry for work.

Another thing is to commit to your pricing, don’t fluctuate or compete on pricing. We both know that you need to start somewhere, but just be careful. Once you have your company built up, you can hold steady on your price and convey that through your value statement. There is value in free, but it should not be a loss leader or cause you to be unprofitable.

When it comes to client meetings, you need to have a scheduling process and decide if you will charge for discovery calls. You can easily spend a lot of times having meetings with clients, and it could take away from your profit generating opportunities.

Kirk says to try to get some money up front for project work. This helps if the client ends up skipping out on you. At least you got paid for the work you did. Once you build a positive reputation and have a great portfolio, asking for money up front should not be an issue for a prospect, it is just normal.

Building a portfolio of example work is important. It should not just be a hard copy or a PDF, you should share portfolio items on social media as well. I mention the book by Matthew Pollard, The Introvert’s Edge: How the Quiet and Shy Can Outsell Anyone, where he discusses how doing business in China is different than in the US. In China, long-term business relationships are the norm. They really do not have short-term contracts. Relationships and trust are crucial.

Using video to communicate can help you build a great relationship and trust with clients and prospects. It makes you more human. Kirk talks about a tool called Loom to talk to clients using video. I mention SoapBox by Wistia.

I asked Kirk what one of the business successes he has had as a business owner. He said that he is proud of the teams that he has built with both companies. We both know that finding talent is very difficult. You need to have employees that are passionate about your cause.

Last, we discussed hiring and finding the right people. Be careful of candidates that self-label themselves as an “expert”. You can teach skills, but not a work ethic, so hiring someone that can learn a skill is appealing if they have a great work ethic and passion for what they do.

You can reach Kirk at and and use the contact us button.

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  • Hank Hoffmeier

    Hank is an author, speaker, podcast host and Sr. Manager of Marketing Operations at Kickbox, a Ziff Davis company. With a passion for all things digital and social, combined with more than 25 years of experience in sales and marketing, he has been dubbed the Digital Marketing Infotainer because he makes marketing fun and successful.