My firm Keenan Reid Strategies builds 9-figure business models and the financial engines behind them. We help enterprise B2B leaders:

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I get the same questions over and over from people starting out.

And I get it – because I asked all of them too. I had to figure it out the hard way — Googling answers, asking around, and testing things in real time to see what actually worked.

So instead of overcomplicating it, I’m just going to walk through the ones that matter most and give you the straight answers I wish I had when I started.

Q: What do I actually need before I take my first client? 

A: This is where most people get stuck, and it’s almost always self-inflicted. At its most basic, you need two things: a contract and a way to send an invoice. That’s it. 

You don’t need a website. You don’t need a logo. You don’t need to “announce” yourself to the world. The people who are successful within 12–18 months didn’t start with any of that. They started by doing the work. Everything else becomes easier once revenue exists. 

But let me make it easy. Here’s a contract template to use – and you can send an invoice through Microsoft Word if you have to. 

Q: Do I need an LLC before I start?

A: Technically, no. Practically, yes. 

You can operate without one, but you’re exposing yourself to unnecessary risk. An LLC separates your personal life from your business life – and it just takes a couple hundred dollars and less than an hour of effort; It’s one of the highest ROI admin tasks you can do early.

This is one of those “don’t overthink it, just go do it” steps. 

We have a piece on how to form an LLC coming up soon, so stay tuned. 

Q: What’s the deal with S-Corps? 

A: This one is very confusing for most people. But to simplify it, an LLC is your business structure, and an S-Corp is just a tax election you make later. 

You don’t need to worry about it on day one. But once you’re making real money – maybe around $75K+ in profit – it starts to matter because it can reduce your tax burden. Until then, keep it simple. 

Electing an S-Corp is as easy as filling out this form. 

Q: Do I need business insurance? 

A: Not right away, but you’ll probably want it. Some clients might also require it. But once you have a steady income, paying for insurance is a relatively small cost for peace of mind. Think of it as one of those “leveling up” moves, not a starting requirement.  

It’s usually less than $300/month and most consultants obtain from The Hartford or Hiscox. 

Q: Do I need a lawyer for contracts? 

A: You can start without one. In fact, early on, it’s often easier to just use your client’s contract. They’ll send it, their legal team will approve it, and you’re off to the races.  

But a lawyer does help a lot in two situations: reviewing your first real contract and creating a reusable template later. We spent about $1,500 on our first contract, which we used for years. It was worth every dollar we paid for. 

Here’s a contract template that we use. 

Q: How do I know if I’m charging enough? 

A: There’s no perfect answer, but there is a way to think about it. 

Start from the top: What do people like you charge in your market, industry, and role? 

Then work from the bottom: What did it actually cost your employer to have you? Salary is just part of it. Add benefits, bonuses, time offs, and overhead costs. It then becomes a much bigger number. 

Somewhere between those two is your range. 

If you want to start top down, you can start by benchmarking rates. On the other hand, you can use our rate calculator to start from the bottom up. 

Whatever figure you get, the next step is to test it in the real world. 

Then you test it in the market, adjust, and refine. That’s the game.

Q: Do I get paid for vacation? 

A: No. That’s the cleanest answer. You’re not an employee, so there’s no paid time off. But that doesn’t mean you shouldn’t take time off, it just means you have to plan for it. This is why your rate should be higher than your old salary. Your rate needs to account for the fact that you’re funding your own time off, benefits, and downtime between projects. Same goes for parental leave. I didn’t get it either, but I did take 13 weeks off.  

Q: How do people actually get their first clients? 

A: This is where people overcomplicate things the most. Your first clients are almost always people you already know. 

My playbook is simple:

That’s it. No funnels. No ads. No fancy positioning. Just conversations. 

Q: But I do a lot of different things – how do I explain that? 

A: You don’t explain everything to everyone, because you tailor the story with every conversation. Think of it this way: you might be skilled enough to solve 10 different problems, but the client you’re talking to only needs one of those solutions – maybe two. So, in any given conversation, you only need to talk about what is relevant to that person. 

That’s how this works in practice. It’s not about narrowing your skills – it’s about focusing your message. 

If you solve three problems really well, then have three separate talk tracks – one for each problem. Then, choose which one to use based on the conversation you’re having with a prospect. 

Q: How much time should I spend on sales vs. actual work? 

A: Almost all sales should be the focus early on. But once you have enough clients on your plate, a good rule of thumb is dedicating 75% of your time to client delivery and 25% developing your business – and that 25% is a non-negotiable, always-on effort. The moment you stop selling is the moment future revenue starts drying up.

If you have long-term, retainer contracts, you can reduce biz dev to 10% (half a day / week). 

Q: Do I really need to post on LinkedIn? 

A: Not in the way you think, because you’re not trying to become an influencer and frankly, you’re not going to bring in clients cold. 

But LinkedIn matters. Think of LinkedIn as your digital storefront. When someone Googles you, they find your LinkedIn profile first so treat it like your own landing page: 

Remember, the goal is to build credibility, not chase engagement. 

Q: What should I actually be tracking financially? 

A: I advise keeping it simple from the beginning by just tracking three things: your profit and loss (money in vs. money out), your tax savings (don’t spend what you owe), and your cash on hand. When you know these numbers cold, that’s enough to run a healthy business early on. You don’t need a complex dashboard. You need awareness and discipline. 

Make it easy and track it in QuickBooks; use a dedicated credit card for all expenses (we recommend Ramp as it automates categorization in Quickbooks, saving you a step later).  

If there’s a theme across all of this, it’s this: most people are trying to prepare perfectly before they start.

The people who succeed start before they feel fully ready — and figure things out while moving.

That’s really the difference.