What does it take to be an Entrepreneur? Join us as Caleb shares his Entrepreneurial mindset and an inside glance at his journey to becoming a successful Entrepreneur.
Caleb is the host of the Podcast Man School and a sitcom writer, currently working on Sullivan and Son, TBS Tuesday nights.
- Caleb tells a lot of jokes, and frankly, some of them bomb. This story is one of those.
Entrepreneurial AH-HA Moment
- We all enter the dip at various points in our life, and those who are able to power through are those who are able to thrive. Caleb powers through his dip during his powerful revelation…
- Caleb is fired up about a lot of things, but his current Podcast tops the list!
Small Business Resource
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Best Business Book
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Since 1996 I’ve been a contributor to several teen leadership development organizations, my favorite of which are the Rotary Youth Leadership Awards (RYLA). I’ve designed and run RYLA programs for more than 2,000 teens in New Jersey and Tennessee.
I credit most of my early managerial skills to these programs. I had to figure out how to build and scale real teams, none of whom got paid a dime, and all of whom were rabidly passionate about what we were doing, namely, changing the lives of teens who came from some of the richest and poorest zip codes in the country (together in the same room).
|Credit: RYLA Maui. What’s cool about this, and really any other RYLA photo is it could be from any of our programs across the world. All of the pictures are the same awesomeness.
Having been immersed in experiential learning programs for some 17 years now, there’s one major lesson I’ve gathered. It happens to be an important lesson for serial entrepreneurs as well.
As soon as you decide your timeline is forever then there’s really no way you can screw up that badly.
At RYLA that meant the other organizers and I looking at each other and committing to be in it indefinitely. As soon as we decided we were going to do these programs for the rest of our lives then making incremental changes each year, even if they seemed major, allowed us to test and review, debrief and change again.
Over time we iterated the program and it got better. Sometimes we came full circle. We got excellent by testing out things that might be not excellent. Some of them were amazing. Some of them were abject disasters. Looking back it had lean startup all over it, except the distance between iterations was a year.
The key was always asking, “How can we do it better?” We even had t-shirts printed with this acronym: HCWDIB?
Imagine then the amazing position of a serial entrepreneur who right now commits to lean startup principles AND at the same time commits to being an entrepreneur forever. If no startup is your first, middle or final AND you iterate quickly using all the amazing technology tools available today, how can you possibly go wrong? You will make it. To do so you will have to keep these points in mind:
- Don’t bet too much on any one iteration.
- Take a break when you need it (maybe make some consulting money or *gasp* get a job).
- Take care of yourself. Work out, eat right, do walking meetings.
- Nurture your network above all else. It’s the only thing you take with you between iterations.
- Learn, learn, learn. Read, read, read.
- Keep notes about each effort and laugh at how crappy you were last year.
That’s what’s worked for me through several disgusting failures and several more break-even hobby-like projects. I have not “exited” nor have I “made it.” I don’t care because I’m in it forever and I will at some point.