10 Tips for Entrepreneurs on Articulation’s 10th Anniversary

It’s been 10 years since I shed the skin of my first business, a traditional PR practice, which I ran for eight years, and then founded Articulation where we unleash leaders through storytelling power.

This means I’m finally an adult – 18 years strong – in entrepreneurship.

So as I celebrate the decade-a-versary of Articulation, I decided to break up my reflections into three buckets. For this blog, I’ll tackle the one about being an entrepreneur. The other two will focus on my favorite stories we’ve coached, and the other best blogs I’ve written worth revisiting.


I listen to at least a dozen podcasts with some regularity. They range from news and politics to storytelling (of course), culture and business. I wish I could take in more real crimes and comedy, but that will have to wait when I’m not also a teen taxi driver.

Last week I caught Guy Raz’s “How I Built This” featuring Steve Madden, the shoe entrepreneur. I’ve never bought any of his shoes (my size 11 feet and 6-foot frame don’t always go well with fashion forward trends), but I certainly knew the brand.

Madden, in describing his dad, who was also an entrepreneur but lived through the depression and generally filled with fear of poverty, said he “Capped his upside,” in his business mindset. In other words, he kept himself from failing but also from wildly growing.

As I thought about it, I never imagined what my business could do- how big or far it could go. I started it simply with the intention of paying my bills when the agency I worked for let me go (and then closed 2 weeks later). And it worked out, so I didn’t stop.

But I also never thought I had a cap. This year we reached our yearly goal in September, which means we either set it too low, got lucky or worked too hard the first three quarters. Probably a combination of all of the above.

As the economy fluctuates with people being forced to hang their shingle and those that want to give it a voluntary try, I’ve assembled my own personal top 10 reflections on what I wish someone had told me about running a business. Some of them are books, some are tools, others are strategies.

The fact is, I love doing it and love learning every year about how to make Articulation more efficient, meaningful, impactful, and profitable. That has been half the fun. Trying, failing, trying again, and finding that flow.

These are in random order as I thought of them. Don’t give them extra weight because they are earlier or later in the list.
Except No. 1.

  1. Before you embark on anything, read the book The E-Myth Revisted. Nothing gets your head more squarely aligned on the imperative balance of working in and on your business. One decision I made the first month I was on my own was to invoice and pay bills on the last day of the month, no matter what. It sound trivial but my graphic artist stockpiles his invoices and send them to me once a year now. I like cash flow too much to stomach that cycle! (More on in/on the business below).
  2. Speaking of cash flow. As soon as you can, get a line of credit. I have only ever used it to “buy my A/R” from myself (i.e. float cash to cover bills when I know I have expected receivables). I’ve never carried any debt more than a month, either. Cash is king, queen and every prince and princess in between.
  3. Decide what you MUST do personally in your business, versus what you can hire away or delegate. I took a long time to realize I really sucked at QuickBooks and bookkeeping. In fact, I would try to save money by doing it myself and then my old bookkeeper would come to my office, sit at my computer and fix my dozens of mistakes without complaint. I realized there are plenty of people good at things I’m not- and they aren’t good at what I do- so leverage them smartly. For me this currently includes a payroll service, tax preparer, bookkeeper, lawyer, graphic artist, SEO consultant, marketing / PR consultant (just because I know how to do something doesn’t mean I should do it), and a EOS / business process facilitator (see below).
  4. Building on No. 3. Make your time first priority and work at leveraging it. Five years ago I made my first real hire. I asked someone to schedule for me. The anxiety I felt looking at my inbox every night after working all day with clients was so much I’d let them pile up. And that meant sales weren’t happening and cash flow wasn’t flowing to its potential. When Kim Goldsmith came on board, her job was to find time for everything important. But instead of only working five hours a week, she now books about 20. And without a doubt, she’s the glue to our business process of getting clients what they need and keeping me focused.
  5. Once you get beyond just yourself and have an employer or two and want to grow, adopt EOS, the entrepreneurial operating system. (Read Traction: Get a Grip on Your Business or Get a Grip to learn more).Heck, when you are by yourself, there are so many tools you can be using. I will not rehash the gifts within that system except to say the last three years of my growth can be directly connected to applying it with great discipline.
  6. If you start to build a team, use Birkman as a personality-at-work assessment to suss out your differences. We refer to our profiles all the time- and it settles so many concerns, questions and anxieties during rough times or conflict.
  7. Leverage technology! My tools I cannot live without today are: Uberconference, Zoom, Pipedrive (we use it as a CRM and project management system), QuickBooks (my bookkeeper likes the online version but the previous one hated it- let them pick), Google Drive (slowly migrating away from Dropbox), OnePassword (how did I keep track of login credentials before it?), the recording app VoiceMemos, an iPad, tripod, light set (for social media video clips), a bag of chargers and dongles for any presentation system connection, a LOGI clicker and of course my iPhone and MacBook Pro. I will sometimes use LinkedIn Sales Navigator, we will add a online document signing tool this year (for contracts- to go paperless), and are adding a learning software tool in February. Oh and my TSA Pre check.
  8. Embrace transparency.  My husband, my team, and sometimes my kids- always know exactly where we are in sales, receipts, highs and lows. My clients get really honest answers about what we can and can’t do for them. And we own up to mistakes and correct them as fast as possible. Bottom line: Transparency is inversely correlated to anxiety.
  9. Plan to work twice as hard and twice as long as you thought it would take. I’ll leave that there.
  10. When you take time off, shut it down. Don’t try to sneak a call, answer emails when you get back. The clarity and energy you need to run a business only comes during those times you aren’t working.


Ruth Milligan Articulation Executive Communication CoachRuth Milligan is the Founder, Managing Director and an Executive Coach and Trainer with Articulation. She is perhaps best known as one of the original curators for any TEDx event (the license program for TED). Since 2009, Ruth has selected and coached over 200 speakers who have taken the TEDxColumbus stage. She is often tapped as an expert in the TED-style of speaking and has authored a class on how to be a TEDx speaker coach. Connect with Ruth.