How To Get Comfortable With Financial Uncertainty

As an angel investor and venture capitalist, a massive part of what I do every day is manage risk.

When I take on investments, I know many of them will fail, and only a few will break even or turn a profit.

Over the years I’ve made friends with uncertainty, and I’ve learned some smart strategies that have enabled me to hold my focus, keep my cool, and, let’s face it, not feel like I’m about to throw up every time risk rears its head.

Now, I know that you’re not here to learn how to become an angel investor or venture capitalist -- you’re here because you believe you have an investable business and you want to learn how to fund your future financial growth.

That said, if you’re serious about growing your business, chances are you’ll be taking a few financial risks of your own.

In this week’s video, I’m sharing my best tips for getting comfortable with financial uncertainty.

Click here to watch it now!

Prefer to listen? Click here:


I'm Kelly Keenan Trumpbour, angel investor and venture capitalist. In this video I'm going to talk about how you can get comfortable with financial uncertainty as you grow your business.

As an angel investor and venture capitalist I have to live with risk all the time. My portfolio is made up of investments where a majority of them I'm betting may not make it to even break even. I've learned smart strategies along the way so that I'm not throwing up every time risk presents itself.

That being said, the risk I live with is nothing like what I see entrepreneurs living with every day. If you're going to give up a paycheck to pursue your dream of a business, you have to learn how to get comfortable with risk and uncertainty.

If you haven't started your business yet, or you're in the early stages, now is a great time to think about the bare minimums that make you happy in your personal financial world. What I'm talking about are the things that you know you need just to survive. If you can provide for these things you'll be okay and you can go about your business knowing that the things that are absolutely essential are provided for in your personal financial world.

This isn't always available to everyone, but if you can try to take some time to grow a cash buffer. It always helps to have a reserve handy in case some emergency comes up or you need an extra month or two of breathing room to carry some costs that you just didn't expect.

I also like to advise entrepreneurs to think about trip wires that will tell them where they are financially and what they can really live with. Think about it in terms of is there a certain dollar amount that you don't want to go past? For example, not spending over $10,000 on a certain business project. Do you have certain ways of feeling that you know that you don't want to change? I've seen a lot of entrepreneurs who get to a place where they can't sleep at night or their stomach is constantly upset. If these things are happening, do you really want to live with them or are they indicators that maybe you need to scale back or reconsider what you're doing.

This may seem counterintuitive but sometimes it's great to take stock of what you could do in the most humble of circumstances. Everyone's capable of taking a job that may not be as glamorous as the startup idea they have, but it'll still pay the bills. When you get into a place of wondering if risk and uncertainty are worth it, remind yourself of what you're really capable of doing. Can you take a job where you're maybe working at a coffee shop? Can you do things on the side that maybe it's not your dream path, but it will give you a paycheck until you get to financial security.

How daring do you want to be in growing your business?

Click here to take my free quiz and find out where you fall in your own risk comfort zone.

Until next week


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