My #1 Tip for All Entrepreneurs (at any stage of the game) - jessdennis.com

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As I’m setting up my 7 and largest business to date, my desire is to bring people along in the process. When I set up my first business in 2008 at 25 years old, I would have loved to have someone to help guide me in that process. It was during this time that I started reading business books and I was blown away by the information they contained at my fingertips but I didn’t have a source like this podcast to truly connect with someone doing what I was doing. 

 

Unlike 2008 where we mostly built behind the scenes, I want to bring everyone along via my blog, podcast, and social media because I love what I do but I know entrepreneurship is intimidating. 

 

The reason I mention how many businesses I have set up or run and for how long is because I wouldn’t start with what I’m doing today. 

Everyone has a different appetite for risk but I can tell you I’m much more concerned with managing the downside than I am about taking risks. Even in this venture, we’re being hypervigilant about managing risk – lease terms, loan terms, other legal paperwork … anything that would stand in the way if things didn’t go according to plan. 

 

And that is my biggest tip for anyone starting a business, care more about managing your risk than crafting all these plans for success.

 

Not that you shouldn’t plan for success, but it’s never been my primary focus. 

 

First and foremost, I make sure that if everything went to hell in a handbasket, that I’d be okay, that my family would be okay. This might feel depressing to think about but it actually gives me tremendous freedom. When I’m not “betting the farm” on one thing, I give myself freedom to play, have fun, be creative, and time to make it work. 

 

WHAT DOES MANAGING THE DOWNSIDE LOOK LIKE?

 

  • It looks like anything that protects you financially IF the business doesn’t work out — if it fails. 
  • How much are you investing in the business? Can you stand to lose that without losing your house, your retirement savings, etc?
  • What are your commitments? If you’re leasing space, what are you committing to, and do you feel confident that you can meet that commitment? In what ways can you mitigate this commitment? (ex:: lease terms with an auto-renew so you don’t lose the space instead of a longer-term lease)

 

DOES YOUR BUSINESS BRING YOU EXCITEMENT OR ANXIETY?

Our anxieties and fears are natural and normal. They are the first things that’ll pop up when we’re getting uncomfortable choosing something like starting a business. Our brains are primal in nature and will always look for fear first BUT when you think about what you’re doing and after the fear subsides … are you excited? Will you be able to sleep soundly at night with this commitment you’re making?

 

I think too often we hold up the entrepreneur as this brave, tough-as-steel person and we think that in order to be successful, we need to be brave and do things other people wouldn’t.

In my experience, it’s stupid to go all-in on something and not manage the downside. I don’t know about you, but the thought of losing my house doesn’t sound fun or brave in any situation. 

 

WOULD YOU BET ON YOURSELF?

I’d bet on myself every single day. I feel more confident betting on myself than I do anyone else, and you should too. 

 

Entrepreneurship and business ownership is my secure path because I’m never putting so much on the line that I could lose it all. Plus, running businesses gives me the confidence that I need and can trust if things don’t pan out. 

 

Think about it … if you lost your job, are you confident you could find another one quickly, in the same area where you live and at the same pay? 

 

The truth is, I’m less risk-averse than most. I don’t lean on traditional employment because I’m really not good at it, but also because I think it’s less secure than running your own gig. 

 

In entrepreneurship, you start to trust yourself. You build the confidence that you can be in control of your paycheck and if anything happens to that paycheck, you can build it again. I’ve done it since 2008.

 

HOW DO YOU START?

You start small; there’s no shame in humble beginnings, it’s how we all start. 

 

What can you bet on yourself? There’s no wrong answer.  How do you build a seven-figure business? You figure out how to build a three or four-figure business first. I always say, if you know how to make a dollar, you know how to make $10,000. It’s the same idea, just more, bigger, leveraged. 

 

Start small. Start where you are. Manage the downside. 

 

This is my seventh business, it’s not where I started. If I had started here, I would have lost sleep every single night. I have no idea how the journey would have ultimately panned out, but I can assure you the journey would have been entirely unenjoyable and stressful. 

 

And the journey is all you have. At the end of the day, it’s not the money that matters;  it’s what you learn and the growth you experience, that’s how you play bigger and get to the next level.

 

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3/17/2021

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My #1 Tip for All Entrepreneurs (at any stage of the game)

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