Five Lessons From Five Years as an Entrepreneur

Five years ago today, I awoke on a sunny Friday morning, rode the Atlantic Station Shuttle to the Arts Center Marta Station, blinked through tears as I strolled through the inviting Woodruff Arts Center Plaza (best commute ever), and arrived at my last day of work. There, my colleagues reminded me what had been so special about my Woodruff career: when I arrived, Alvin Townley had tucked a goodbye card and bouquet in my office. My friends Claire Dempster and Jennifer Williford threw a bittersweet goodbye party. The CEO himself, Doug Shipman, even made time to come say a few words! I departed the place that had shaped a big part of my identity since I began working there as a college intern—and I headed directly to an evening fundraising event for Magenta’s first client, Meals On Wheels Atlanta.

The next four years were basically the same kind of whiplash —jumping from adventure to exhilarating adventure to learn how to best manage my company, deepen my subject matter expertise, and cultivate my business. Honestly, I was pretty overwhelmed a lot of the time. But this year, something changed: I had gathered enough experience to know where Magenta adds the most value, and I focused my energy there. Working with my teammates at Rootstock, I took time to reflect, repackaged our offerings, and rewrote our website.

SO! To celebrate Magenta’s five year anniversary, I’ll recount the five most important lessons I’ve learned and how they shaped “Magenta 2.0.” Most importantly, I’ll unveil our glorious new site!

Here I am pictured with a special edition Magenta Anniversary friendship bracelet hand-crafted for me by my (new!) husband. It has beads spelling out “MAGENTA” and five little pink stars, one for each year!

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Lesson 1: Put the Big Rocks First

My first anecdote took place earlier this year at an Entrepreneur’s Organization Accelerator meeting when our facilitator introduced the metaphor of “rocks” as priorities. (The concept was popularized by The 7 Habits of Highly Effective People.)

Say you’re trying to fit various sized rocks into a bucket: if you start with pebbles, you’ll fill up the bottom of the bucket and have less room for the rest of the rocks. Conversely, if you put the largest stones in the bucket first, the pebbles can trickle into the empty leftover gaps, fitting more content into the same amount of space.

Similarly, in our day-to-day, it’s SO easy to let tasks and distractions pile up, stealing our attention from the important goals we set over longer time horizons. Often, though, our biggest priorities are the solutions to the pressing, ongoing challenges we face—if we started by tackling those, some of the minutiae would disappear. (Easier said than done!)

During that EO meeting, I realized Magenta’s website was my biggest rock. It needed a major facelift to illustrate our (pretty niche!) service offerings. Because the site wasn’t adequate, every time someone asked me what Magenta does, I had to create an explanation, dig up a relevant example, and write up a unique proposal or case study to sell a project. Yet I couldn’t find the time or energy to attack our out-of-date website. (Look up the cobbler’s shoes syndrome.) It got to the point where I dreaded inquiries because they were so disruptive to my weekly client engagements. That is not good! To grow, I had to get that big rock out of the way…and to get that done, I needed help.

Enter the energetic, grounded, and perceptive team at Rootstock who helped me add definition and process to everything we do! Together, we codified Magenta’s offerings, assembled a portfolio of work, and project-managed our fabulous new website to completion.

Check it out to dive into the wonderful world of fundraising communications and learn about Magenta’s magic touch ✈️

To celebrate getting this massive rock out of the way, here’s a photo of me trying to move Bubble Rock at Acadia National Park—the “unmoveable stone” which has been tilting on the edge of a cliff for thousands of years. I have no doubt that if Ryan and Terra had been pushing with me we would have toppled it together!!

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Lesson 2: Showcase Your Unique Expertise

When I worked at a nonprofit, I was rewarded for doing many different things well.

Then, I launched Magenta—three months before the onset of COVID-19. Naturally, as work became scarce during the spring of 2020, I had to jump on any business prospects that came along. I took on everything from grant writing to social media management, but I didn’t have the processes in place to support so many varied services. So, I ended up with about 20 different jobs. As I suffered personally from burnout, my business suffered from unclear offerings and mixed messaging.

All along I thought Magenta was growing. It was my mentor David Feldman (pictured here) who first challenged this mindset. When we first met, he was preparing to publish Small by Design, a book describing how small companies leverage agility and specialization to deliver more value than their large competitors. To do this, scrappy businesses need to identify their most impactful offerings and position themselves as the leader in that area by telling a story demonstrating their unique expertise.

David writes: “As a small by design company, you need each project to serve a larger story: one of who you are and who you are becoming. A story of the crises you confront for your clients…A story of the value you deliver and the visions you make real.

When you tell that story well, in a way that connects to the needs and ambitions of your clients, they don’t care if you’re a company of one or one thousand. They care instead that you are the one who understands their unique needs and has proven you can help them succeed.”

For Magenta, putting this into practice meant assembling a portfolio that illustrates the work we do best…but also letting go of some work that wasn’t serving our larger story. We honed our offerings to areas where we add the most value (Impact Reports and Cases for Funding) and referred work outside that scope to other trusted, specialized partners.

If you visit our Services page, you’ll see that every offering links to a relevant example in our Portfolio, and each service supports our mission of helping nonprofits demonstrate their impact to funders.

Lesson 3: Create Your Own Momentum

Admittedly, there is some nuance involved with positioning your business in a specialized niche. Crafting a story that demonstrates your unique specialization may require some creativity and risk-taking.

My friend and EO Accelerator groupmate Darcie Adler gifted me a book titled The Obstacle Is the Way, which includes an anecdote about how Amelia Earhart began her career as a pilot. Naturally, my attention was captured—I’m an Amelia Earhart admirer because of my mom’s career as a pioneering woman in aviation (Captain Mom and I are pictured here).

But, I didn’t know the following story about Amelia:

“It was the 1920s, and people still thought that women were frail and weak and didn’t have the stuff…

[Amelia] couldn’t make her living as a pilot, so she took a job as a social worker. Then one day the phone rang. The man on the line had a pretty offensive proposition, along the lines of: ‘We have someone willing to fund the first female transatlantic flight…You won’t get to actually fly the plane, and we’re going to send two men along as chaperones and guess what, we’ll pay them a lot of money and you won’t get anything.”

The chapter goes on to describe how Amelia took the offer, insulting as it was. Paraphrasing, the point is that people who defy the odds know if they can get a little momentum, they’ll make it work toward their goals.

Sometimes, it can be tough to find the clients who need your niche offering AND are willing to pay what it’s worth. When I was starting up and developing my track record, opportunities to write impact reports were essential to building Magenta’s brand. I recognized that those opportunities were worth more to me than the impact reports themselves were to my potential clients.

Now, I’m not saying you should work for free—but there are ways to negotiate a win-win partnership that don’t require a huge cash fee. In one case, I traded an impact report for admission to a course. In another, I agreed to take a client’s urgent grant writing work on the condition that they also retain Magenta for their impact report. In another, I had written so many grants for a client that I was able to knock out a case for support in a few hours, so I did—not because the client needed it, but because my website did! As my portfolio grew, so did my expertise and my reputation.

Now I’m in a position to charge a premium for Magenta’s work, but only because I have a robust portfolio that demonstrates the value of our services.

In closing, another gem from The Obstacle Is the Way: “Just because the conditions aren’t exactly to your liking doesn’t mean you get a pass. If you want momentum, you’ll have to create it yourself.”

Lesson 4: Automate, Delegate, Eliminate, and Refer

I learned about the book Chillpreneur on a list of recommended reads from It All Media way back in 2021 and it was exactly what I needed. For the first time, I learned that entrepreneurship doesn’t have to be a miserable grind! Chillpreneur introduces lessons to create a life of abundance without endless hustle. I wanted a business that fulfilled my life, not one that sucked all the time and energy out of it. (Pictured here is my cat, the ultimate “Chillpreneur,” at his desk.)

Step one in creating a business that fulfilled my life goals was finding my unique offering. Step two was freeing up my time to focus on delivering that unique offering.

How to get rid of tasks that keep you from focusing on your one-of-a-kind value-add? Automate, Delegate, and Eliminate—and I like to add, Refer. (For the record, I’ve now read about this philosophy in numerous other books like 10X Is Better Than 2X and Buy Back Your Time—but I read it in Chillpreneur first.)

Some tasks can be automated: I invested in software (Monday.com, Quickbooks) to set up and schedule processes at the beginning of each project. Now I’m already scheduling invoices and blocking time in 2025.

If a task can’t be automated, you may be able to delegate it. I made a mistake the first time I tried this! I wanted to build a business centered around writing, so I hired writers. Instead of doing the work I like to do most (case writing), I was doing all the stuff I should have been delegating, and wearing so many hats it was impossible to think strategically or lead. I know this makes me sound like an idiot, but other entrepreneurs know it’s easy to fall into this trap!

Some tasks can be eliminated altogether: I started by refocusing on Magenta’s unique value-adds, created clear-cut product offerings that support our value proposition, and I eliminated any projects that did not fit in those product scopes. Even though I let go of some revenue in the short term, I referred each of those projects to a trusted partner and set up referral agreements that have generated more revenue for Magenta. (Which is why “Refer” is critical!)

I currently have a list of things I hate doing, things that interrupt my deep work, and things others can do better or faster than I can. Though I can’t immediately afford to delegate all those things, I’m starting with the cheapest tasks and working my way up the list. Most importantly, I have time, energy, and enthusiasm to develop the written content for every project, meaning clients are getting my superpower poured into all their deliverables.

On the Magenta About page, you’ll see we have a growing list of partners who support us on our projects. We also refer business to them if it’s outside our scope.

If you’re not sure how much to spend on automation and delegation, keep reading…

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Lesson 5: Implement Profit First Money Management

I will leave you with a super practical lesson: Profit First accounting.

I’ve always been a  “saver” and set aside 10% of everything my company made from the beginning. The book Profit First takes this philosophy a step further by setting targets for your company’s Profit, Tax, Owner’s Compensation, and Operating Expenses, all as a percentage of revenue (simply Google “Profit First percentages” for a recommendation of what those percentages should be).

Instead of taking on expenditures and looking at how much you have left over as Profit, Profit First flips the script so you’re looking at how much you have to spend on Operating Expenses after you’ve set aside funds for Profit and Taxes. An excerpt from the book:

“Profit first sparks faster growth because it makes you reverse engineer your profitability…When you take your profit first, your business will tell you immediately whether it can afford the expenses you are incurring, it will tell you whether you are streamlined enough, and it will tell you whether you have the right margins.”

This philosophy changed three behaviors in my business to hire and spend more wisely:

1. I right-sized Operating Expenses: with a blueprint for what percentage of Magenta’s top-line revenue to invest in delegation and automation, I built a more sustainable expense ratio. (The ideal ratio here varies according to company size and circumstance, but I keep mine below 35%.)
2. I started paying myself a more reasonable wage instead of taking the peanuts left over from my bloated Operating Expenses. I previously thought that I needed to invest heavily in staff to grow, but since I was the primary person delivering Magenta’s services, investing in myself was the most important driver of Magenta’s growth.
3. I used the money saved in my Profit account to build a reserve, pay myself bonuses, or invest in special projects, like my new website.

As your company matures, there may be good reasons to take on debt or make a risky hire to grow the business. However, even when I do invest a larger percentage of revenue in a certain category, I do so intentionally, understanding the effect on the other areas of my business.

Profit First is a great starting place that companies large or small can address today to cultivate real value from their businesses.

Pictured here: a photo of my desk from my last day at The Woodruff Arts Center. My coworkers decorated my office with flowers and gold coins…symbolic of all the money I’d be making as an entrepreneur! 😁

Conclusion: There’s Always More to Learn

After five years as an entrepreneur, the one thing I know is this: there is always more to learn! Knowledge sharing is key, and whether you do that through accountability groups, mentorship and coaching, reading business books, or tracking your own journey, you can jump start your company’s growth by learning through experience (your own experience and the experience of others). Magenta has gleaned valuable insights through the trials, errors, and insights of other entrepreneurs. I hope the lessons I’ve learned so far have passed a nugget of wisdom on to you.

Of course, the journey continues: I’d love to learn from you and hear your thoughts. Connect with me on LinkedIn to keep the conversation going.