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How to Win (Nearly) Every Time

Updated: Feb 10, 2020

I speak to a lot of student entrepreneurs, and someone always asks some variation of “how did you get/earn/find ________?” No matter what they're asking about, I usually can distill it down to two main points: 1) Play the Odds. 2) Just Ask.

I know, it sounds super fucking simple. “Duh, Paul. You have to do the work to see the reward.” But I think so many of us forget that it IS simple (I include myself in this pool, 100%.) We want the answer to success to be complicated or plain luck because then we can justify failure upfront and why not "to attempt."

We want the fallback (it's complicated and expensive), the scapegoat (I just have bad luck) as if there's some magical recipe for reaching our goals that we don’t know. Maybe that’s a cultural problem or a human brain problem – I’ll leave that part to the experts. But here's the part I do know:

It took some time to build the self-awareness to realize that I am my only real obstacle (say that slowly to yourself: I AM THE OBSTACLE), but even before I started our company, I was naturally putting into practice both "playing the odds" and "just asking."

Playing The Odds

Create a goal and break it down into yearly, quarterly, monthly, weekly, daily, maybe even hourly steps. Statistically, if you commit to those small steps, you will see a higher level success. Now, don't kill yourself when you aren't disciplined. The trick is to get back on track faster every time. Don't worry about being perfect, worry about pushing yourself to get back on track. Every salad you eat, every email you send, it all adds up.

Here's a good example: when I was looking for a college advertising internship, I knocked on every Ad Agency door in Lincoln and got turned down. I was begging people to hire me to mop the floors (for real). Going from a highly recruited division 1 athlete to not being able to get an internship was a genuinely humbling experience. How could Clint! not remember my name, I'm applying for an internship, dammit?! Ha. Getting shot down by a dozen Nebraska Ad Agencies for a free internship or mopping duties was a massive ego blow for me. It made me angry. My competitiveness kicked in, and I was determined to get the best damn internship I could.  I decided to send these elaborate packages with my resume to the most significant ad agencies and the coolest brands. It took painstakingly creating and sending 300 packages to get a reply… from Nike. BOOM.

I was playing better odds contacting 300 NYC Ad Agencies versus 12 Local Ad Agencies. Bonus, I had more options when it came to working with cool, big brands.

Raising venture capital for Bulu Box was much the same. I only pitched the “perfect” investors, so I didn’t do a lot of pitches, and we weren’t getting terms sheets. It took my genius co-founder and wife Stephanie reminding me of those 300 packages I sent for my internship to kick my brain into gear. I did a complete 180, pitching as many VCs as I could find. I knew they wouldn’t all be a fit for Bulu Box, but the practice helped me improve my presentation skills so that when I did present to the right VCs, I had the confidence to close because I had experienced everything.

I was playing better odds pitching 500+ Investors versus 10 "perfect" Investors Local Ad Agencies. Bonus, the practice built my confidence. 

Just Ask

This one is simple, and my mother taught me this. You never know unless you ask. We preach this at Bulu Box, and it’s resulted in major gains for our clients and our team. (I’m talking big things like million dollar investments and national TV appearances… plus, the small things like a whiteboard or an afternoon off.)

I believe most people don't ask due to the fear of being told no and the embarrassment that comes with that. I am forever grateful to my Momma because one of the billion things that brilliant woman taught me was to get over myself and check my ego. Truth be told, we only get 1% of the things we ask for, but that 1% is how you get on national TV. 

Now...go write down some goals, build a plan, play the odds and just ask! What's the worst that can happen? A little embarrassment? Meh, whatever. What's the best that can happen?

Ya, that's rad. Go get it. Don't stop. Never stop.


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