When I got my captain’s license, I worked on a boat in mission bay that held 150 people. My boss encouraged me to invite my friends for a free trip. About a dozen took me up on the offer. Right before getting underway, the owner told everybody that there was a two-drink minimum. A can of Soda was $5, and a can of beer was $9. I’d never felt more ashamed than to have offered this free boat ride to my friends. This bait and switch method felt so dirty. I vowed to have honest pricing when I bought my own boat. I quit that job in mission bay and bought my own boat a week later.

I don’t upsell. I don’t have any “fees” or hidden costs. If you pay for a trip with me, the entire experience is included. Tax, port/marina fees, drinks, snacks, pictures, and souvenirs are on me. I don’t want to bait people in with cheap prices, fake discounts, or cheesy advertising.

Most companies in tourism devote a considerable amount of their budget to marketing/advertising. I don’t. I never will pay someone to paint me in a good light. I don’t spend a penny on advertising. If my customers enjoy their experience, I hope they tell their friends. This means I can deliver the best product at a reasonable price.

A private sunset trip is $400, not $399. It’s insulting if a business owner thinks they can trick anybody with this silly psychology.

Tomorrow, I could double my prices, then list them as half off on a site like Groupon. I would immediately start to sell loads of tours. Even after Groupon takes their massive cut, I would be able to turn a profit. But I feel like this goes against everything I believe in.

My business model has not paid immediate financial dividends, but I’m in this for the long haul. Aside from August 2017, I’ve lost money every single month I’ve been in business. This year I’ve already invested in a bigger boat, and I’ve spent a ton of money to make it nice. I’ve spent more money on it than I grossed for the entirety of last year. I’m going all in on Randy Phillips Tours.

I’ve paid myself a modest salary and taken enough time off to keep my relationship amazing. I’ve also continued to travel. The perspective I gain traveling, keeps my mind fresh, opens me up to new ideas, and gives me an optimistic view on humanity.

This isn’t my first full time business venture. I ran a scooter rental business in Pacific Beach the summer of 2015. It made so much sense on paper. The fact was I hated it. People were always tearing up my equipment, I felt like a full time maintenance guy, working for an increasingly negative paycheck. At the end of the summer, I pulled the plug, and walked away. I had previously spent 5 1/2 years of active duty in the US Air Force. I saved half of every dollar I made. Suddenly my life savings was gone, and I was back to square one.

When I decided to go all in on Randy Phillips Tours, I didn’t crunch the numbers. I maxed out my credit cards, got some more, and maxed them out too. I had a gut feeling that if I did what I loved, others would notice, and that would the key to running my first successful business. It has been much harder than I can imagine, but 18 months in, I can honestly say I love it more than ever.

I am optimistic about the summer ahead. It will be do or die for Randy Phillips Tours. I am really counting on the awesome customers I’ve had over the past year. If everybody who has a great time just convinces a single person to take a tour with me, I’ll be OK.

By Labor Day 2018 I’ll either:

Have had a busy summer and considerably chipped away at my mountain of debt.


Be 28, completely bankrupt, and satisfied that I followed my heart.

Either way, I’ll be happy.

Thanks for allowing me to live my dream. I’m so ready to see what 2018 has in store.

If you have friends or family in San Diego, send them my way. It means so much to me.

Randy Phillips