Let’s get tactical: What software tools do you need?

by | Sep 30, 2020 | Software | 0 comments

Today, we’re going to get a little tactical. Software has been a huge pain for dozens of entrepreneurs I’ve met, and it’s hard to know what to invest in, and when. 

I hear a lot of statements like this:

“I pay for so many different kinds of software, and the cost is really adding up.”

“I bought this because my friend uses it and loves it, but I just don’t get it.”

“I keep hearing about new tools coming out, and I don’t know if it’s something I should get or not.”

If you’re ever in that spot or know someone who is, come back to this email. It will help you identify what you need, when to get it, and how to use it for free for as long as possible.

Let’s start with software tools that every business owner should have (and how you can use them for free):

A bookkeeping system and invoicing tool

  • Check out Wave, which tackles both your books and your invoicing. You can automatically import your transactions here, categorize them, and get reports. At the bare minimum, you need to know your revenue, expenses, and net income, and Wave will help you do that.

A dedicated bank account

  • You have to dig a bit, but free business bank accounts do exist and are worth finding. I haven’t yet found any reason to pay a bank every month just to have an account with them. No matter what, you need a completely separate bank account for all business income and expenses. Azlo is a good first option to check out.

An email address and a calendar with the ability to send invitations

  • You can start out with a free Gmail email account and just upgrade later to a paid domain email with G Suite. The Google calendar can be easily customized to your preferred settings and added to your phone.

A contract signing system

  • HelloSign lets you send three contracts per month for free.

An email marketing system


  • Most people can use their free version of Canva for quite some time without an issue. Canva is an easy to use design software that will allow you to make social media graphics, PDF covers, and anything that needs to be prettier than what you can create in Word.


  • Until you regularly have long (over 40 minute) meetings with more than three people, you can use the free version of Zoom just fine.

Cloud storage

  • Your Gmail account will give you enough Cloud storage to get started.

Project management system

  • The free version of Asana is plenty for most people and will help you track your tasks and priorities.

As you grow, you’ll find yourself adding a few more tools and upgrading to paid versions for your original tools:

Website and domain

  • Wix, Squarespace, and WordPress are the three biggest players here. WordPress is the most powerful but also needs the most knowledge and maintenance, and Wix and Squarespace are both easier but more limited.

Calendar system

  • Calendly’s free version can work well if you only want one type of event and basic functionality (i.e. a 30-minute call), but you’ll likely start paying for your calendar tool relatively quickly. Acuity is another great option.

Password manager

  • LastPass has a free version that can work if you don’t have ongoing contractors or a team, but you’ll want to start paying if you do. This tool will save you so much time trying to keep track of your passwords, and it’s much more secure than stashing them in a spreadsheet somewhere.

YNAB (You Need A Budget)

  • YNAB is hands down the best budgeting tool on the market for entrepreneurs and will help you start doing responsible things like saving and planning ahead for your expenses.

Video and screen capture tool

  • Loom allows you to seamlessly record videos, including screen share videos, that are great for communicating with contractors, clients, or your team. There is a free version, but if you use it often, you’ll need to upgrade.

Time tracker

  • Toggl’s free version is enough for most people and will help you evaluate the profitability of your projects and understand how you’re really using your time.

Depending on your business, you may need one or more of these also: 

Workflow system

  • 17hatsDubsado, and Honeybook all allow you to completely automate your onboarding process, and they all include forms, email templates, contract signing, and invoicing. If you onboard more than a few people per month or want to have a really slick, professional process, these can come in handy.


  • CRM stands for customer relationship manager…it’s an annoying acronym for a tool that will help you track your prospects and networking connections. Pipedrive is one of my favorites and very affordable.

Social media scheduler

  • Hootsuite will let you schedule 20 posts per month for free, but if you’re very active on social media, paying for a scheduler might make sense.


  • We use Typeform for professional looking forms and a more complex automated quiz that we share with our audience. If you don’t have long quizzes, you can use Typeform for free (Google Forms is also a great free option).

Integrated marketing tool

  • As your marketing efforts get broader, you may start to look at integrated marketing tools like Ontraport. We don’t recommend these until you’re over $250k in revenue.

Course tools

  • Course tools like Teachable and Kajabi are great if you sell information products; otherwise, you can probably live without them.

It’s a big list, isn’t it? If you have a lot of tools in your business, you’re not alone, and you’re not doing something wrong. You’re running a business – it’s part of the gig!

My biggest recommendation is this – get the most minimal tool or plan you possibly can, and don’t buy annual plans until you’ve paid for a tool for several months and know you will keep it. Once you do commit, put on your blinders and ignore all new shiny tools! Only add a new one to your roster when you’re actively missing it on a day-to-day basis.

As a reference point, A Squared currently budgets around $3,000 per year for all of our tools (about $250 per month). We’re careful, but we’re willing to invest in what we need.

I’m curious – is there anything you’d add to the list? Anything you’d take away?

P.S. If you want to dive deeper, check out these great insights from Brad Eisenberg of BE Lean: How to Spot the Best Free Tools and How Not to Get Burned by Them.