Starting a Business is Scary as Hell

Last night, I spoke to a room of hundreds of people who want to turn their passion into a business. It was electric, as usual, because this topic turns me on like crazy.

We dug into the top four fears people experience when starting a business, and this article is a mini-masterclass breaking each of them down:

1. Not knowing which business to start  (ack!)
2. Where to find the damn time and money  (oof!)
3. When to quit your job  (eek!)
4. How to do sales (yeep!)

You ready?

Question #1: How do I know which of my passions to turn into a business…and furthermore, what if I don’t even know what my passion is?

Some coaches might ask you this: "If money were no object, what would you do all day?" to uncover your passion. I personally don’t love that question because – let’s get real – money IS an object. At least it is right now. So, my advice is to start the business that people are willing to pay you for TODAY.

Ask yourself this question instead:

"What am I the go-to person for? Where are people already asking for my advice and input?"

Are people always asking you for life advice? 👉 Maybe it’s coaching or advisory services.

Do you always get tapped for team-building events at work? 👉 Try event planning.

Are people curious how you get so much shit done every day? 👉 Create a "get shit done" workshop and charge for it.

What you may find is that the universe is already screaming at you to start this business. And remember, this is simply the initial version of your business, the one that gets you up and running and cashflowing. It WILL morph and change over time, so don’t get too attached to version 1.0 of your business being "THE ONE". Just start.

Question #2: How much time and money do I really need to start a business?

Simple answer to the money question: You need almost no money to start a business…but you need a good chunk of money to quit your job and run it full time.

Deeper Dive: If you start a service-based business (consulting, coaching, design, etc.) then you need almost no money to start. Just your LLC, a contract, and a few cheap software subscriptions. So just start already, will ya?! All that said, I insist you have your financial ass cheeks covered by the time you quit your job…otherwise you’ll be freaking out about money and running back to corporate after 3 months. Use your Side Hustle money to stack your savings account so you can quit with some swagcurity (swagger + security).

Simple answer to the time question: Plan for 8-12 hours a week to run a successful Side Hustle.

Deeper Dive: These 8-12 hours are easier to plop on your calendar than you think. For example, you can do 7:00 – 9:00 AM three days a week and 4:00 – 6:00 PM the other two days a week. Roughly half of that is for client delivery and half is for business development.

The harder part is protecting those hours from your boss, your family, and any other demands on that time. You’ve got to disclose your business to your boss and get firm agreements on your new working schedule…otherwise they will blow you up per usual and c*ckblock your business. Set these same agreements with your spouse on childcare coverage + chauffeur duties.

Question #3: When can I quit my job? Should I take the leap or take a more calculated risk?

I’m a fan of the (mostly) calculated risk. Ask yourself this:

"What would need to be true in order for me to submit my resignation?"

For most of my people, the answers are "liquid cash in the bank" and "a handful of clients to prove this is a viable business." Once you have those two things, you can take the leap and know it’s not a total shot in the dark.

Question #4: I’ve never done sales and it freaks me out. How does that work?

Same here, my friend. I never sold a thing in my damn life. So, don’t make the same mistake I did by cold-messaging hundreds of strangers on LinkedIn. Just, no. 🤢

Let’s use attraction-based marketing instead, and here’s what you need:

1. An extremely strong point of view that cuts through the noise
2. Social media posts that express that point of view
3. Visibility moments (webinars, roundtables, speaking engagements, masterclasses, etc.) to invite people to

If your posts are slappin’ and people are engaging, then it’s natural to invite them to your next gathering…and that is a warm, wonderful way to connect with people instead of a cold "boner-poke" in their DM’s.

Are you starting to feel that "holy shit, maybe I can DO this" feeling? Yeah, me too. If so, we should talk. Click below to snag a time on my calendar and we can jam out on your business idea. I can't wait to meet you, badass!