Carrie Richardson

Co-Founder at Richardson and Richardson

Carrie Richardson is a serial entrepreneur who specializes in helping technology companies introduce new products and services into the North American reseller partner network. Her client list includes Cisco, Datto, Huntress and Sophos. She is a partner at Richardson & Richardson Consulting, a consulting firm that will change the world by helping 1000 entrepreneurs achieve and realize their visions.

She has bootstrapped and sold two outbound sales development agencies, and supports new entrepreneurs through mentorship and microlending.

Carrie is an advocate for workforce re-entry, creating sales training systems that support reskilling and upskilling non-traditional job candidates for technology sales development roles. She shares this system with agencies that are focused on government subsidized on the job training programs, and helps companies implement her program.

Her next volunteer project includes co-founding “2 Seats”, a volunteer-led community that will amplify the authority of women in technology by connecting influential technology marketers with female speakers and content creators.

Carrie has two amazing daughters. She and her husband Ian live part time in their off-grid stealth camper, “Penny The Van”. Her goal is to never be cold, which is hard to accomplish living in Michigan.

You can learn more about Carrie online at, and connect with her on Linkedin in at

Where did the idea for Richardson and Richardson come from?

My husband and I both owned and operated small businesses before we founded our consulting practice. He owned an IT consulting firm, and I owned an outsourced business development agency. Both of us worked with hundreds of small business owners. Most struggled with sales, marketing, and strategy. They made expensive errors; delegating or outsourcing things well before they understood them. Richardson & Richardson was built around the idea that if you want something done right, you have to do it yourself – but you don’t have to do it by yourself. We want to help 1000 entrepreneurs build their vision and change the world.

What does your typical day look like and how do you make it productive?

My typical day begins around 4 A.M. I’m not a keener, I’m an insomniac.
I read, write, hit the gym, walk the dog and start my “real work day” around 8 or 9.
I keep my days productive by keeping all phone notifications disabled and blocking off my calendar to external access on Mondays or Fridays. If I’m buried, those are catch up days. If I’m ahead, they become long weekends.
Most of my days are very predictable, everything in our business is processed out, so I have tasks and activities that I am responsible for and checking them off of the list is quite satisfying: that magic list keeps me on track. As a visionary, I could spend my whole day in “what if” fantasyland – a checklist keeps me focused.

How do you bring ideas to life?

I used to overwhelm my team with ideas.  Eventually, they figured out that if they demanded an implementation plan along with the idea, I would only put forward the ideas that were important enough to me that I would follow a structured process to evaluate and present them.  I learned a pretty great opportunity evaluation process through the Goldman Sachs 10,000 Entrepreneurs program – each new idea starts with identifying the characteristics of the opportunity – for me, I consider:

  1. Does it solve a customer pain?
  2. Is it a new product or service we’ll offer to our current market?
  3. Is it a current product or service, but targeting a new market?
  4. How does it build on an existing competitive advantage?
  5. Does it have the potential to be profitable?
  6. Does it fit in our current strategic road map, or is it something to purse later?

Then I take the ideas that fit to my leadership team, and they decide which ones I should spend more time evaluating.

What’s one trend that excites you?

I’m excited that employees are refusing to work with companies that don’t value them, and hopeful that trend leads to more entrepreneurs. There are so many programs available to people who are interested in building a business now – incubators, accelerators, economic development agencies offering grants, programming, and mentors – there’s never been a better time to start a business in the US!

What is one habit of yours that makes you more productive as an entrepreneur?

One habit I’ve developed that makes me more productive as an entrepreneur is the “two minute rule” – If it is going to take me two minutes or less, I do it immediately instead of pushing it off until later.

What advice would you give your younger self?

The advice I’d give my younger self is prioritize what I think about my choices over what “other people” will think about them.

Tell us something that’s true that almost nobody agrees with you on.

Unpopular opinion: we’ve created an entire ecosystem that encourages the goal of building big businesses with no regard to profitability as fast as they possibly can using other peoples’ money. We aren’t rewarding people for building innovative products, or quality services; we’re encouraging people to copy things that already exist with the sole purpose of an “exit” to the company they copied.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I call people every day. I think everyone else should, too. Real phone calls to real people. Phone calls are great for asking for advice, generating referrals, or for establishing a relationship that will earn you the right to ask someone for their business. If you count up the amount of time you spend “researching” before you try to interact with someone, I think you’ll find you’re wasting more than ¼ of your day just messing around on social media with no actual KPIs to determine if that time is being well spent or not.

What is one strategy that has helped you grow your business?

Data hygiene is the cornerstone of our business success. Early on, we made asking the same three key questions mandatory on every call we made, regardless of what kind of client we called for. We incentivized our employees to gather those data points. Now, creating targeted marketing campaigns is simple and sales forecasts are incredibly accurate.

What is one failure you had as an entrepreneur, and how did you overcome it?

One failure I had as an entrepreneur was a “do as I say, not as I do” attitude with my team. They had to follow process, but I did whatever I wanted. I realized a few years in that your employees take their cues from your actions, not your words. If it’s not important enough to me to follow the process, should it be important to them?

What is one business idea that you’re willing to give away to our readers?

If I was going to start a business right now, I would start something with no, or very little capital investment that I could do as a sole provider from my home first. I think to be an industry leader in your city for most services you’d really only need to show up on time and do what you’ve promised to do in order to run circles around most human-powered businesses – I’d SEO it aggressively against the dozens of gig-economy platforms that don’t seem to have any quality control or issue resolution. Here are a couple off the top of my head:
• pet-related services (boarding, walking, grooming, house-sitting)
• home companion services for busy adults with aging parents (wellness and support visits that didn’t require dispensing medication, but did include support with housekeeping, meal prep, guided physical activity, and any other errands that could relieve the burden of people who are already stretched thin caring for their kids AND their ageing parents!)
• lawn care and seasonal yard clean up
• housekeeping or commercial cleaning services

What is the best $100 you recently spent? What and why?

Personally, the best $100 I’ve spent recently was on microfiber towels for our off-grid conversion van. When we travel we shower at at 24 hour gym, and they’re amazing – they dry fast, they don’t leave lint on you, and they came with carrying cases – they fold down super small and are easy to pack. Professionally, the best $100 I’ve spent was on branded laptop stickers that I include with any thank-you card I send. People post them online after receiving them – they cost so little and people love them!

What is one piece of software or a web service that helps you be productive?

I’m a big fan of using all of the features of any software we’re already paying for – and Microsoft Office365 has a ton of features that are overlooked for productivity – bookings, for example – it’s free with your o365 license, and it replaces paid solutions like Calendly. We use it to allow people to self-schedule meetings, but we can also put qualifying questions right into the form that provides data to help us determine how the meeting should go.

What is the one book that you recommend our community should read and why?

Atomic Habits, by James Clear changed how I approached achieving goals! I used to be a “I’m going to do everything differently…starting next Monday” kind of person. Now I focus on making small, incremental changes immediately that build towards larger goals. For example, I wanted to focus on getting fitter this year, but I was having difficulty getting to the gym every morning at 5. Not because I don’t like going to the gym, but because I had to many barriers to getting there. The first habit I built wasn’t “get up at 5”, it was “don’t keep your phone near the bed so you don’t check your email first thing”. Then it was “make sure your gym clothes are ready the night before so you don’t get frustrated and waste your workout time looking for matching socks and clean shorts” and then it was “have coffee when you get back, not before you leave.” I recommend it to anyone who has tried any feast and famine approaches to behavior modification.

What is your favorite quote?

I stole this from my first mentor, and I use it a lot – I think about it as it pertains to employees AND clients:
“FIFO” (fit in or f off)

Key Learnings:

  • Routine and process is the key to productivity
  • Your cell phone is a tool that should be used for your convenience, not to facilitate convenience for others.
  • Data is your most valuable asset.
  • Connecting with other people “live” is essential to growing your business – using the phone will improve your communication skills.
  • New habits are easier to form with incremental improvements instead of big sweeping cold turkey changes
  • There are profitable businesses that can be started by anyone at any age with zero capital investment.