- The Jill James
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- Oops, it’s my 10-year anniversary
Oops, it’s my 10-year anniversary
Life moves pretty fast
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Fly like an eagle, let my spirit carry me
This week, I’m thinking about the immortal words of that eminent philosopher, Ferris Bueller:
"Life moves pretty fast. If you don't stop and look around once in a while, you could miss it.”
With the end of school and the political drama playing out in Los Angeles this week, I almost cruised right past my tenth business anniversary.
My business started over lunch. After a failed negotiation of maternity leave from my job, I waddled my 7-months-pregnant self into Tavern in Brentwood. I walked out with a commitment from my first client. Shoutout to Amber Allen of Double A Labs for being a trailblazer.
While the pandemic ate my five-year plan, I’m not missing out this time. About 35% of businesses make it to the 10-year mark, and less than 15% of women-owned businesses make it to my level of revenue. As one of my mentors said, you’re successful if you’re still here.
But that’s not the thing that I’m most proud of. I’ve noted before that I was both an excellent and terrible employee. Because I got laid off so much, my income history looks like I was interval training.
Since I started my company, I’ve never not paid myself.
Ten years of never missing a payroll. Closest call was in the second year, when I got distracted by someone else’s vision of a content business and a full-time job offer with a fancy title. I solved for that lull in my pipeline by selling my car and getting deadly serious about monthly pipeline tracking. That’s about the time I started this newsletter.
Ten years of making it work around being a caregiver. Working from hundreds of locations around the world, from my parents’ basement to Paris’ Left Bank. I went fully remote in 2017, long before the pandemic, after stressing over yet another late daycare pick-up in the molasses swamp of traffic between Santa Monica and downtown LA. And I found my centering principle: we always show up for our people.
Ten years later, I’ve worked with thousands of small business owners, from those laying the groundwork to leaving corporate to securing multi-million dollar exits. The highs, lows, pivots, tears, celebrations. And all the days we hauled ourselves out of bed, showed up, and kept things going.
Does this business look like what I expected on the first day? Not a bit. Do I want my life to be any other way? Burned those boats a long time ago.
Whether it’s your first day or you’ve been an entrepreneur forever, take a moment today to celebrate that you’re here and you’re doing your thing. What’s your next milestone, and how will you celebrate it?
Thank you for doing all the things that keep me going: opening this email every week and giving your encouragement, feedback, comments, sharing, and likes. Thank you to my advisors and partners for listening, advice, and valuable time. And thanks to my clients for trusting and paying me.
Thank you to my kiddo for asking me what my job is and saying, “Mom, yikes, that is WAY too hard.” Every time I start to drift back toward overprioritizing work, or doing it more conventionally, you remind me why I designed it around life with you.
If you’re curious about how I got from Day 1 to the present, I talked to Erin Austin about it this week on her podcast, Scaling Expertise. Check out Episode 113 on YouTube, the Think Beyond IP website, or the podcatcher of your choice.
June Dates to Remember
June 15: Estimated Tax Deadline. This is the second quarterly estimated tax payment for 2025, covering income from March 1 to May 31. If you’re not in a FEMA-declared disaster zone, your payment is due by Monday, June 16. Make sure you’ve scheduled payments for both federal and state if applicable.
June 19: Juneteenth federal holiday Juneteenth is our newest recognized federal holiday. As a private company, you are not required to recognize federal holidays. But if you are open, make sure you understand the local, state, and federal holiday wage requirements for hourly and part-time employees, and you run your payroll on time.
June 24: Anthology Release Day. I’m honored to be one of the contributing authors in the new anthology The Wisdom Collection: Stories That Transform How We Live, Connect, and Lead available June 24. This book brings together voices from entrepreneurs who’ve chosen the path of impact, strategy, and resilience. You can save the date in your calendar here.
July Compliance Check: Are You Ready?
July 1 brings a fresh wave of state and local compliance changes:
Minimum wage / minimum salary increases in Alaska and Oregon (plus specific cities and categories in California)
If you’ve been heads-down running your business (or serving clients who are), now is a good time to check that your compliance house is in order. Get clear on the rules that apply in your state via this interactive map from VestWell. If you’re new to options for offering your own retirement plan, my 2025 small business guide is available here.
Media Kit
Are Manufacturing Jobs Actually Special? From another public service I love, Planet Money explores whether manufacturing jobs can really be the difference-maker in the US economy. Punchline: in the present day, it’s the unions, not so much the specific jobs. The series delves into the kinds of jobs and training needed for a healthy economic future.
For your very remote work. You’ve undoubtedly found yourself in an area with no cell service at a critical moment. Wired reports on Meshtastic, an open-source project that enables text messaging without cell service or Wi-Fi. Using affordable radios and unlicensed frequencies, it creates a decentralized mesh network ideal for emergencies or off-grid communication. You can DIY this tech from the link above, or keep an eye out for future commercial options.
The Milli Vanilli Effect: By now, you’ve undoubtedly seen eerily realistic AI video from Google Veo 3. What does that have to do with 1990’s best new artists, Rob and Fab? Fakes evolve, and we learn to spot them. On Blusky, Mark Cuban predicted that convincing AI-generated video will push us offline and back into the real world. Verify before you share or take action. If one person says it’s raining and another says it’s not, remember that you can check what’s happening outside.
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