Alright – so today we’ve got the honor of introducing you to Piper Watson. We think you’ll enjoy our conversation, we’ve shared it below.
Piper, looking forward to hearing all of your stories today. What’s something crazy on unexpected that’s happened to you or your business
Life had been pretty crazy for me leading up to March of 2020. In 2018 I left the nonprofit makerspace that I co-founded, feeling lost, burned out, and totally confused as to what to do next. So I vanlifed for 2 years and 8 countries, with 2 not small dogs, to try and find my answers. What I found was that people continuously coming to me for business and life advice since I had successfully been running multiple creative businesses for 10 years. So in February of 2020, my husband and I settled in a new city and I officially launched as a life and business coach. I quickly secured a six-month contract worth half a year’s salary to coach an entire leadership team for a community acupuncture franchise. Then, the world stopped. One month into our coaching engagement, the CEO called me in tears that because of the pandemic, they would have to close the doors to all three of their locations indefinitely. She was understandably terrified and heartbroken at having to lay off her entire team of 40+ people, and just like that my entire revenue stream disappeared. Which, surprisingly, wasn’t the primary thought. My initial reaction was that I knew I could help her. I had spent an entire year training as a coach to help entrepreneurs be able to manage their mind and their emotions along the roller coaster of running a business. So I told her to just continue with me one-on-one, totally for free, for one month so that she could at least have some unbiased support to help her figure out what’s next. It wasn’t easy. My own financial worries needed to be dealt with as we had incurred moving costs, were still trying to get settled and now both my husband and I were out of work. So we both just did what needed to be done, we swallowed our pride around our experience and higher education degrees and he got a job packing boxes at Amazon and I got a job stocking shelves at Trader Joe’s. Even with that, it still felt like the right thing to do to offer my client free coaching in a whirlwind of global chaos, grief, and uncertainty. So she and I got to work in my off hours at Trader Joe’s. I helped her feel all the feelings and brainstorm all of the possibilities. Two weeks in we had come up with a way to completely reinvent her business using some of the culture and ethos that I was surprised to learn at Trader Joe’s so that her business could operate more streamlined, cost less, and be more FUN for everyone involved. So when she received a large and unexpected grant to open back up in May of that year, she brought me on as a full-time coach for her and her staff to help everyone transition into this new business model and collaboratively create a healthier work culture that all were inspired to participate in. The pay was nearly double our original contract so needless to say, I didn’t stay at Trader Joe’s for too much longer after that. But it just goes to show that when you that in any business, when you show up in service and focus on delivering value to people, the money always comes and things always get figured out.

Piper, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I found my way to coaching after realizing I had a knack for starting successful businesses out of my passions. My first business was a lifestyle and wedding photography business, which led to co-founding a nonprofit tool lending library and public makerspace. That fueled my DIY passions for making and interior renovations so from there I had an Airbnb business and now I coach other creatives and entrepreneurs on all things life and business! Because when you’re self employed it all bleeds together and it can be hard to carve out time for things outside of running your business like your health goals, fun with friends, or just to put your face in the sun for 20 minutes when it always feels like there’s more to get done and never enough time. And one thing I discovered through hiring my own coaches for either business or life, was that very few coaches do both from the unique perspective of living the LIFE of an entrepreneur. More importantly, over the last 17+ years of being self-employed I’ve realized that this is a mindset AND strategy game. It doesn’t make any sense to have the most amazing social media strategy on the planet that you paid thousands of dollars for if you aren’t feeling confident enough in yourself to BE visible online. So one of the things I’m really good at is helping people do things like get total clarity on their business; who they serve, what they offer, what their unique gifts are, and how to use that in authentic marketing that doesn’t feel icky and gross. I help them gain more confidence in who they are as a business owner – that it’s not just a silly hobby, and that they DO know enough to be successful! I also love helping people learn the tools to stay consistent with showing up in their business, no matter what’s happening in their lives, so that the entrepreneurial journey doesn’t feel like a roller coaster of action and exhaustion -it’s just slow and steady. I typically work with people 1 to 1 or in groups depending on their goals. One of my groups is only for Career Clarity, while another is just for people starting their businesses. And the main thing that I want people to know about my work and the thing I’m most proud of is that I had ZERO prior experience in any of the industries I started businesses in, and was STILL successful. All to often people hold themselves back from dreaming and doing big things because they think they need to go back to school, or get another certification, or take a ton of online classes – when the truth is you just need to start. But of course that’s easier said than done and what I do is break down the exact tools and steps needed to “just start” ANYTHING.

How do you keep your team’s morale high?
The best way to manage other humans and maintain high morale is to BE A HUMAN. Meaning, ALL humans are designed to want to connect – even my introverts out there! We all WANT to be seen, acknowledged, appreciated and loved. So, take the time to get to know your team – what’s important to them both in and outside of work, not just the names of their kids or pets. Become a great listener by listening to understand, not just listening to respond. It’s a skill you can totally learn and it has a positive ripple effect in all parts of your life! AND learn how to manage your own vibe because it’s literally the cologne or perfume that you wear. People will smell it a mile away and it will either attract or repel them. Meaning, take the extra time to ground yourself before coming into work if you’ve had a rough start to the morning, have emotional support systems to be able to vent your frustrations in a healthy way and to the appropriate people – NOT your team, and work to grow your communication skills to be able to confidently navigate any situation with more ease. Also, and this might be the most important thing – bring the FUN. Not that work is a party all the time, but it can be enjoyable 99% of the time and it’s your job to create that culture!
How did you put together the initial capital you needed to start your business?
With my first business as a photographer, I bootstrapped it! I was 25 and barely had a credit score so most of my equipment needed to be purchased in cash. So I waited tables, assisted other photographers by slugging around their lights and gear, and moonlighted as an editor from an ad off Craigslist just to afford a basic kit. Then, as I began building up my credit score and history by paying off my bill in full and slowly requesting credit limit increases that I could reasonably swing – I started growing my kit to include gear that allowed me to be even more creative. I kept things lean by only buying used equipment (except for camera bodies) and selling anything I didn’t use in a 12 month period.
By the time I was ready to start my second business, I had such a sky-high credit score that I was able to leverage that as our start-up capital until we secured grant funding. And even then, I would still use credit for our regular operating purchases and pay it off in full every 3 months or so as we built our revenue streams through classes and membership. I repeated this process with my 3 and 4th businesses as well and I know a lot of people would shudder to think about using credit but my philosophy is money is money whether you’re paying “rent” on it or not. Don’t judge where it’s coming from because that’s just keeping you stuck longer!
Sure there are business loans out there but credit was just faster and easier for me to manage. I certainly don’t advocate going out and applying for allllll of the 25% APR credit cards. But if you have the discipline to create a pay-off plan and know your business revenue can easily support that, by all means go for it! Just know yourself and be brutally honest or you could get into a pickle.
Contact Info:
- Website: https://piperwatson.com/
- Instagram: https://www.instagram.com/thepiperwatson/
- Facebook: https://www.facebook.com/piper.watson
- Linkedin: https://www.linkedin.com/in/piper-watson/
Image Credits
Photos and creative by Piper Watson

