How I Built A 7-Figures Coaching Business [And Created The Best Planner Ever]

Published: December 16th, 2022
Jennifer Dawn
Jennifer Dawn Coa...
from Rhinebeck, NY, USA
started September 2014
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Hello! Who are you and what business did you start?

Hi there, I’m Jennifer Dawn and I own a business coaching practice, a digital marketing agency, and I’m the founder of Best Planner Ever. I serve business owners who are working to hit their first six or seven figures of revenues and I help them to grow their businesses without sacrificing their personal lives.

I didn’t go to school for coaching - my experience comes from learning in the trenches with my own companies (I started my first “real” company when I was 23) and a natural desire to help others succeed. The first year I began my business I made $50k in revenues and now we are at seven figures.


In my own business, I was tired of getting burned by marketing companies and saw it happening to my clients. That’s why we took on the task of vetting out quality, reliable people who know what they are doing and do the work.

What's your backstory and how did you come up with the idea?

I didn’t come up with this idea the traditional way, in fact, I resisted this business. I was asked to lead a national network of women entrepreneurs and agreed to do this in exchange for equity in the company and a small salary. I did grow the company I tripled revenues - but when it came time for my partner to honor the equity agreement - she made up a lot of excuses not to do so.

When it became apparent she was not an honorable person and just using me - I resigned and went out on my own. Luckily, many of the women I had been helping followed me and my coaching practice began. It was emotionally devastating for me to get used by my partner, but also a blessing in disguise starting a business with paying clients from day one.

I’m also very grateful for my former position because it genuinely gave me the confidence to coach. I had grown multiple seven-figure businesses - both on my own and in corporate - and didn’t even realize just how valuable this experience was. I’ve now discovered this is my purpose and passion and love the work I do. It’s what inspired me to create our marketing agency which further supports our business coaching clients.

We now have a full range of products to fully support any business owner working towards their first seven revenue figures. From our time management system (Best Planner Ever) to our coaching academy, coaching team, and marketing agency. We offer the kind of help I wish I’d had along the way!

Take us through the process of designing, prototyping, and manufacturing your first product.

I launched the Best Planner Ever in 2015 as my time management tool. I had been using numerous planners, sticky notes, journals, etc., and could not find one tool that did everything. That’s what inspired me to create the daily planner. I began using it for myself, then with my clients, and then finally as its product.

Every year I would make a few small changes to the planner, but now the layout and format are tested and proven. If I made too many changes there would be a huge backlash! I don’t fix anything that isn’t broken so I leave it alone now.

After I created the planner, I wanted to develop online content that business owners could use at their own time and pace. This is what inspired me to also create the Jennifer Dawn Coaching Academy. We now regularly add to this amazing library each month with our monthly live training classes specifically designed to help business owners.



If you can’t be found on google when the clients you are looking to work with are trying to find you, you’ve got a problem.

Describe the process of launching the business.

I never formally “launched” my business. I didn’t even have a website for the first 6 months I was in business. It was all word of mouth. Once I decided it was going to be for real I did develop a website. I hired an amazing woman from my past networking group to build out my website and she did a fantastic job. That website lasted about 8 years without any changes and truly stood the test of time.

It wasn’t until our product offering expanded, I added more coaches to my team, and the marketing agency that we needed to develop a new website. We’ve now done this and the even better part was this time around we used our agency to develop the new site.

I learned many valuable lessons while launching my businesses. I also bootstrapped all my companies because in my earlier years I was never “bank eligible” and so I learned early to figure things out and make it work with the financial resources I had. Not to say there’s anything wrong with bank financing, but if you can’t get funds that way just know it doesn’t mean you can’t still launch your business. You can, and you can be very successful without a bank loan.

Since launch, what has worked to attract and retain customers?

Since I started my business nearly a decade ago there have been some tried and true practices that have contributed to our success.

First, is our digital marketing and online presence. The world has changed. People don’t go to the yellow pages anymore to find what they need, they “google” it. If you can’t be found on google when the clients you are looking to work with are trying to find you, you’ve got a problem. We’ve always invested in our SEO, Google Ads, website, and online presence to make sure when a business owner is looking for a great coach, we’ve done everything we can to get found by them.

Once we have the client - we take care of them. Our retention is unheard of in the coaching industry. We have clients that stay with us for years - because they are getting VALUE. Not because we locked them into a contract.

We meet our clients where they are and take steps to make it easy to work with us. To be honest, we treat our clients the way we want to be treated - which sounds easy and obvious - but it’s not. In today’s crazy world it can be easy to lose sight of the simple things like basic common courtesy - but we routinely hear from our clients “you are the coaches I’ve been searching for” and that means so much to us.




How are you doing today and what does the future look like?

Our operations today are going strong. We are now offering more online options such as our 7 Figure Roadmap Series which is an online course where we teach everything a business owner needs to do in their business - from top to bottom - to set themselves up for success.

The first year of running our Agency was tough on profits. Getting all the pieces in place and vetting the right contractors was intense. There are so many contractors out there who make big promises and then don’t deliver. You end up having to clean up their messes - which is never fun. However, we started the agency for this very reason. In my own business, I was tired of getting burned by marketing companies and saw it happening to my clients. That’s why we took on the task of vetting out quality, reliable people who know what they are doing and do the work.

We are really happy with the team we have now and very proud of the marketing we provide for our clients. Any new business will lose money at first, just so long as that doesn’t continue forever.

The future looks strong and our business model is perfectly aligned with the needs of our clients. The longer we’ve been in business we’ve continued to refine the offering and service and now we are in a position to fly.

Through starting the business, have you learned anything particularly helpful or advantageous?

Business growth is personal growth - without question. In my 25+ years as a business owner, I’ve seen so much. Good and bad. I’ve been blindsided by employees and partners, had clients stiff me on their bills, and seen employees make big promises only to find out they misrepresented their skill sets.

I’ve also created massive results for our clients and had days where I thought it could not get any better. Having my business has also helped me get better at setting boundaries. With my time and health - because it’s so easy to just focus on nothing but work.

I love having the flexibility to work from home. I can be on a client call one moment and then still be able to pick my kids up from school. My morning commute is walking up a flight of stairs to my office. Being a business owner means you get to decide how you want to live and work. I love that freedom and flexibility - some days I do have to remind myself I have that power!

What platform/tools do you use for your business?

Our favorite business tools include:

Because I have a background in software I’m a big fan of technology and automation.

What have been the most influential books, podcasts, or other resources?

Books that have helped me the most include:

… and so many more. I read 1-2 new books every month.


Advice for other entrepreneurs who want to get started or are just starting out?

The best advice I have for business owners just getting started is to get help… BUT… it should be the right help. I so often hear stories about entrepreneurs going into massive debt or depleting their retirement accounts or maxing out all their credit cards to pay for coaching. Any coach who encourages you to do this is not on your side. There is plenty of help available today that can be accessed with reasonable investments. As you get larger and have access to more funds, then absolutely invest more in coaching.

What you don’t want is the “investment” to be so enormous you are worried about the money the whole time and can’t focus on the coaching.

Do your research, talk with several coaches, be picky and choose one with that you have a good rapport. Once you choose the right coach, show up and do the work. The clients who get the most success are the ones who decide they will. It’s not enough to just hire a coach.


Where can we go to learn more?

If you have any questions or comments, drop a comment below!