Meet Will Cobb

We caught up with the brilliant and insightful Will Cobb a few weeks ago and have shared our conversation below.

Hi Will, thank you so much for opening up with us about some important, but sometimes personal topics. One that really matters to us is overcoming Imposter Syndrome because we’ve seen how so many people are held back in life because of this and so we’d really appreciate hearing about how you overcame Imposter Syndrome.

There were a lot of questions in there to talk about!

Imposter Syndrome and dealing with “nay sayers” are hand and hand for us.

Me and my wife started our company Cobblestone Productions (now Cobblestone Weddings) as a way to get out of my (Will) state job and the grind from that but also because we were passionate about video and photo. We then took the shaky road to pursue creating a production company around these passions shooting weddings at first and edging into the corporate world as well. It took 5 years for us to both be full time with it and quit my state job. We could have left earlier but the imposter syndrome took over us. Our skills were honed but we didn’t think we could charge the real numbers we needed to make a true living from it. It was also scary to leave the state job with great health care and stability. Ultimately it was a great choice and the freedom we gained was amazing.

There is so much to that story but That is the gyst. We worked for 3 years with Cobblestone as our sole income. Every year we worried if we were charging too much or too little or if we were going to book enough gigs. I think that it was a struggle but we always made it.

Another thought on this is going into how college played a part in sort of locking us in for a time. Millennials felt like they had to go to college after High School and thus you had millions of kids too young to know what they wanted to do pursuing things they didn’t like and racking up student debt. Then you finish college and don’t like what you are doing but you have to do it to pay back the debt. That was us for sure. We luckily put our heads down and paid off 67k in 2.5 years but it was daunting and one of the reasons we felt the nay sayers like our parents and peers telling us that quitting a state job and security to pursue our own thing really kept us at the state job longer than we needed to be. Breaking that mold was freeing and proving to everyone we could strive on our own was also freeing.

In a crazy turn of events. All of this led to our ultimate dream of sailing the Caribbean for a time. We left everything behind last summer and live on a catamaran in the Bahamas with our 2 girls 2 and 4 yo. It was super great and refocused us on our life goals and desires.

We are just now returning to California to continue our wedding business, focusing specifically on weddings now and starting a few new brands. I also am taking up the state job to help our transition back, as we spun things down when we left. We have a new found desire to really expand the business rather than riding it and hoping it worked out. We are super in the pocket now and focused on our goals

Thanks, so before we move on maybe you can share a bit more about yourself?

Cobblestone Weddings is our Wedding photography and videography brand. My wife and I started it 8 years ago as a general production company but have focused it into the brand it is today: Husband and Wife duo capturing weddings. We are passionate about working together and capturing peoples love wedding after wedding. We write all the music for the wedding films too which is pretty great.

Outside of weddings, I am an Entrepreneur and have pursued Software and other small company ideas that I will be expanding on in the next years. Several in the wedding space to help couples capture their wedding. We have an app we are working on for capturing short video clips of guests saying kind things about the couples. We also do some point and shoot camera rentals.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

Obviously we needed the video and photo skills to be good at our job, but really the Wedding Photography and videography space needs these skills:

– People Skills: You have to be incredible with social and people skills to crush at any vendor role in weddings. A couple is booking you to be with them on one of the most important life events they will have. You have to be fun, easy going, and relatable. People skills outside of weddings can help with getting promotions and wining and dining your customers or employers. If your a fun person to be around, you are more likely to stay around.

– Adaptability: You must adapt or die. This is in anything you do. For weddings, you must be flexible and adapt to timeline changes, drunken party members, lighting changes, or whatever a 10 hour multi location, indoor and outdoor live event can throw at you. For other fields, it is the same. Don’t let AI kill your job. Adapt to it and learn it and crush your job.

– Obsession: I used to teach guitar to kids and the biggest thing I saw was if they were not obsessed with wanting to learn they would not succeed or well, they wouldn’t do that well. They could learn it okay but they wouldn’t be great. If you want to be great, be obsessed. This is even the model seen in Amazon’s corporate structure. They always talk about customer obsession. If you want to win, find a way to be obsessed about what you do, and additionally make your product something your customers will be obsessed with.

What would you advise – going all in on your strengths or investing on areas where you aren’t as strong to be more well-rounded?

I am a generalist on many things just due to the nature of running my own business. I need to know everything because its just me and my wife. I think investing in learning more things to make your business succeed is super important and then when the money is flowing and that is taking too much time away from actually making money, then you outsource it. We just outsourced or finances and I think that was a great step.

My buddy went the route of, from the beginning, outsourcing the things he didn’t know. It worked out for him, but it is costly. I think I am a little tight with that stuff, and I have probably an unhealthy mentality of “I can figure out anything”. If that isn’t you then outsource. You can learn anything on youtube these days though.

Contact Info:

• Website: https://cobblestoneweddings.co/
• Instagram: https://www.instagram.com/cobblestoneweddings/
• Linkedin: https://www.linkedin.com/in/1willcobb/