Episode 113

E113: Work Less, Grow More: Jill James' Blueprint for a Self-Sustaining Business

What if the biggest thing holding your business back… is you?

In this episode of Scaling Expertise, I sit down with Jill James, founder of The Jill James, a fractional COO firm that helps expert founders scale without burning out or staying stuck in operator mode. Jill built her firm by asking one powerful question: “How can I help people do the work they love without being buried in admin?”

We dig deep into the invisible costs of overwork, the identity shift from doer to leader, and the moment Jill realized she needed to break her own rules to scale. If you’re feeling like your business can’t run without you, this episode is your wake-up call.

Jill shares hard-earned wisdom from scaling businesses to $10M+ and offers actionable ways to reclaim your time, build operational clarity, and let go of control—without compromising your vision.

Key Takeaways:

  • Founders can be the bottleneck. If your business can’t function without you, it’s not scalable.
  • Don’t sell your time—sell your thinking. Experts grow when they stop doing and start designing systems.
  • Scaling isn’t about doing more—it’s about doing less, better. Create space so the business can operate without you.
  • You don’t need to be a “visionary.” You just need to be clear about where you want to go.
  • Resist the "fixer" urge. Let your team solve problems so they can grow into their roles.
  • Fractional leadership. This can help expert founders transition out of operator mode with structure and sanity.

Jill is a featured author in The Wisdom Collection: Stories That Transform How We Live, Connect, and Lead—an anthology of powerful insights from business leaders who’ve built, failed, and figured things out the hard way so you don’t have to. Each chapter is practical, quick to read, and full of hard-won wisdom.

The book launches June 24 and will be available for just $1.99 during its first 24–48 hours.

Want the launch link or more details? Check out Jill’s announcement post on LinkedIn.

Resources Mentioned in the Episode:

🔗 Check out Jill’s firm: The Jill James

📬 Get her insights: Subscribe to the newsletter

🤝 Connect via Beehiiv

More About Our Guest:

Jill James is CEO & Founder of The Jill James. As a recent client summed up, she is what would happen “if you could hire Sallie Krawchek, Dany Garcia, and Mackenzie Scott to run your company.” Jill started her career in New York City as an investment banking analyst with J. P. Morgan and personal wealth planner with AXA Financial (now Equitable). She moved to tech start-ups and held nearly every non-programming job in early stage companies, including product, marketing, sales, and C-level leadership. She used these experiences to found The Jill James in 2015, and now partners with self-funded founders to grow and run purpose-aligned companies.

At the University of Chicago, she earned a BA with honors in Political Science from The College and an MBA in entrepreneurship, strategy, and marketing from Booth School of Business. Originally from Greenwood, Wisconsin, Jill lives in Los Angeles with her kiddo and their very squeaky guinea pigs. She writes a weekly Beehiiv newsletter for owner/operators of small businesses. Learn more at thejilljames.com, including a video introduction and our most recent newsletters and blog posts.

Connect with Jill James:

Charity: https://www.wearebgc.org/

Connect with Erin to learn how to Turn Your Expertise into Scalable Recurring Revenue.

LinkedIn: www.linkedin.com/in/erinaustin/

Think Beyond IP YouTube Page: https://www.youtube.com/channel/UCVztXnDYnZ83oIb-EGX9IGA/videos

Music credit: Paphos by Mountaineer

A Team Dklutr production

Transcript
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Hello everyone.

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Welcome to this week's Scaling Expertise,

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where we talk to experts who have scaled

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their expertise and also have some tips

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about how you can scale your expertise.

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I'm very excited for my guest this week.

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The Jill James, I love that.

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Who is a business consultant who helps

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her, founders go from founder to CEO.

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So welcome Jill, so much.

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Thank you, Erin.

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Thanks for inviting me.

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I'm very excited to have you here today.

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you talk about is so applicable to

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this audience, but before we dive

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in, would you introduce yourself?

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Sure.

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So I'm Jill James, as you mentioned,

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my company is called the Jill

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James, not gonna get lost there.

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so my focus is kinda in three areas.

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I'm a business manager, I'm

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an operator, and I also have a

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background in wealth management.

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so that makes it a little bit unique

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in that, I mostly work with self-funded

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people and, whole different set

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of, Tools that we have when you

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are not having venture investors.

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So that's really, an area that I've

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chosen to focus in to help people who

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wanna self-fund their businesses and

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grow them to the right size for them.

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So I think our conversation today is

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gonna be very applicable to your audience.

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Absolutely it is.

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And I'm gonna jump right in with what

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you mentioned there about your target

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audience, about them being founders

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that aren't gonna take VC funds.

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And we're gonna talk about scaling,

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we're gonna talk about intellectual

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property, but I'd like to just start

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with how the misperception generally.

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That when we talk about scaling,

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we're talking about VC funding

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and we're talking about software.

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We're talking about these things

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that we read about in magazines

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as opposed to the things that

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we do every day in our business.

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Have you found that kind of

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general misperception when

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you're talking to people?

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Yes.

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Mm-hmm.

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in my working background, I come

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from investment banking, wealth

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management, and venture backed startups.

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Mm-hmm.

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And you can see I am not in that world.

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Right.

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So it's.

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What can we take from that world?

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But if we follow that playbook, and

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that is a lot of what you see in

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the press, that is a lot of what you

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see on social media is the get big

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fast playbook or the assumption that

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there is unlimited capital or you've

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just been handed a chunk of money.

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And you can go try some stuff out

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and figure out how it works before

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you have to sell anything to anybody.

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that isn't the real world

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for 98% of businesses.

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Mm-hmm.

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So, you know, as much as we look

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at, we hear about these venture

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capital businesses and it's sexy

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to say, oh, they got 1.2 million

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in funding, or they got mm-hmm.

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You know, 50 million in

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funding, whatever it is.

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sometimes that's just to figure

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out what are we gonna sell?

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Yes.

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And

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that isn't the reality for 98% of us.

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And I think in particular, if you are.

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a non-traditional founder, or you

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didn't go to a certain set of 10

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or 12 schools where you met the

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people who are gonna fund you.

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Mm-hmm.

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you are going to start your business with

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money that you earn by selling things, and

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then you're gonna earn the right to borrow

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money from other people or from banks

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mm-hmm.

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To accelerate the growth of your business.

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It is a very different playbook and I

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think, what I am seeing is more people

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are evolving to, I want to keep control.

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Of how this business grows and I wanna

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do it at a pace that's right for me.

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Mm-hmm.

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And not what somebody else dictates.

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And so when you choose that path to

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be self-funded, we have to be very

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intentional, especially from about.

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250 to $500,000 up to about 5 million.

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we have to be extremely intentional

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in how we step through that time

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to help you grow, without falling

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into some of the traps that are

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gonna start to come into your world.

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Around seven figures, where lots of

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people start to say, oh, I can help you.

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Now you made it to seven figures.

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You're in the big leagues.

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Well, let's get you on

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this different playbook.

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the foundation that it takes to build

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a self-funded business and to set a

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playbook for yourself is really what we

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work on with founders in my business.

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Thank you for that.

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Thank you.

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So having set that framework,

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let's go back a little bit.

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You okay.

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Mentioned you came

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from, the venture world.

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How did you make that transition

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to where you are today working

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with this population of clients?

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Yes.

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That is a good question.

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So for a long time, being in, I think

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I worked at seven different venture

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backed startups over my career,

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and been through lots of exits.

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And so I was always looking

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for what is that big idea?

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what is the idea that

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would get me venture?

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Mm-hmm.

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And

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I had a lot of other ideas.

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That I didn't follow because they

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would not have qualified for venture

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and they were probably all really

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legitimately good businesses where

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I would've made a lot of money.

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Mm-hmm.

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But I did not understand

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how that worked yet.

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I understood the get big fast model.

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Right.

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That was business school.

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That was all the businesses I worked in.

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That was the goal.

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So when it finally came down

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to it, I ended up leaving.

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I was the COO of a venture

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backed tech startup.

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And I was seven months pregnant there

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was a conversation about maternity

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leave and it did not go well.

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And so it was about

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no

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leave.

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Maybe it was, it was about no leave.

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It was about no leave.

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So I waddled my little self out of there.

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I took a minute to get organized and

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I had had a number of people, I had

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partnered with more, Founders who

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had come from a place of knowing how

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to sell, having a good idea about, a

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community or a business that they could,

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establish, but no operational expertise

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in how to set up and run a business.

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So I had, self-funded founders who had

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seen me do that, and they had left the

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door open of, if you ever wanna do this.

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Fractionally or maybe would take

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a side job where you're not all

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consumed with building somebody

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else's business, I would hire you.

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So I called a couple of those people

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and I said, this is the situation,

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and I'm gonna be having a baby.

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But you know, until then.

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We can start something and

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then we can pick it up again.

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And they said, any help you could

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give me, I would just so appreciate

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having someone look over my shoulder.

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Help me out with this,

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and whatever we can do.

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And I really appreciated that

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because the first couple of years

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in my business I've worked very

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flexibly, more like a fractional COO.

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Mm-hmm.

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I think this is.

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Part of the process of especially

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an expertise business, is you're

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gonna try out a bunch of stuff.

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I tried to work with

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different kinds of people.

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I worked on an hourly basis.

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You know, I just kind of

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figured out like, what is this?

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What are people asking me for?

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You know, that was almost my investment

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in finding my product market fit.

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in the evolution of that, about two

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years in, I saw an opportunity with

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lots of women who needed flexibility.

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Who are establishing businesses because

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of that often around caregiving.

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And so I redesigned what I was doing

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to make it a little bit more package

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driven, knowing those women were probably

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not going to get venture just given

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the numbers and the kinds of businesses

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they were establishing moved more in

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a direction around, how do I work with

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self-funded founders and what does that

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mean and what's my unique expertise?

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That I can bring to that area.

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Like what have I learned and

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the people around me, how can

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they help these people as well?

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so that was really the evolution.

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This was 10 years ago, right?

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Mm-hmm.

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My son is nine and a half.

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It was almost this time, 10 years

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ago that this conversation happened.

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Mm-hmm.

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10 years later, I have a very defined,

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this is who we are, this is what

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we do, this is who we're for, and

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these are the reasons that we do it.

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All of that is very well developed at

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this point, but I went through a phase

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of experimentation initially where I

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just got paid to show up and mm-hmm.

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Do my old job as you know, my business.

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And that's a perfectly

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legitimate way to start.

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Absolutely.

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Thank you for sharing that

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because so many of us, you know,

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there's so much information now.

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Yeah.

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And it is really easy to get

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caught up in all the different, way

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offers and ladders and all these.

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Things, and I have

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absolutely suffered from it.

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I'm, post corporate who mm-hmm.

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now works with a different population and

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it has taken, it is, I'm still evolving.

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Frankly, I'm, I'm not 10 years out

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working with this group of people.

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learning who your best client

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is, the best way to help them.

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Our expertise can be used in lots

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of different ways, but you know,

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the more we work with people,

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the more we hear their pains.

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The more we start to speak their

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language, the more it makes sense.

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Like we can start to drill down on

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the best way to help them, and that

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you're probably not gonna just.

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Come straight out of, this corporate

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for most of us, and go straight

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into the final product, so to speak.

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So, yeah.

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Yeah, I think that's a great point that,

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there is going to be an evolution in

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your entrepreneurial journey even if

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you're a product-based business mm-hmm.

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The first idea that you have.

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If you're very lucky, it

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will be the successful one.

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Mm-hmm.

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But in most cases, there's a pivot,

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there's some amount of learning,

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there's a change in the market.

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And so we have to continue to look

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for the opportunity and move toward

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it as we learn more about, you know,

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ourselves and what our capabilities

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are and, who wants to work with us.

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Now when you think, of course,

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this is a scaling expertise Yes.

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Uh, podcast.

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So, a lot of people have a very narrow

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definition of scaling as being mm-hmm.

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You know, selling books or courses

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or software, things like that.

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But what does scaling mean

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to you and your clients?

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Yes.

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So scaling in the self-funded

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world is a very intentional act.

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Mm-hmm.

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It's about milestones and it's

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about knowing what are those

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points of investment and the

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next place we're going to land.

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So scaling often as you start

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as a self-funded business owner,

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there's the problem of where is

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the money gonna come from, right?

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So we need to be intentional of

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looking at where are we going next?

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How much money is it gonna take?

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What are we gonna have to sell?

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who else do we need on the staff?

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What other resources do we need?

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And sometimes that means there's gonna

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be a dip where we need to move forward

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and we don't have the revenue yet.

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Mm-hmm.

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So, where are we gonna get that capital?

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Is it, from a bank loan?

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Is it from a line of credit?

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Is it a seven a loan?

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Learning that world of places that you

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can borrow for growth, that you know

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you can pay back because you're moving

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through a point in time and not stuck

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in, I don't know how to get out of this.

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Let me borrow some money.

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it's meant to accelerate you.

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So I think that is, the thinking

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on scaling is not how fast

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can we get, how big, but.

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What's the next iteration of

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this business where we can be

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profitable at this size and deliver?

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Mm-hmm.

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And how long is that gonna take?

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How quickly are we

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gonna move through this?

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Because what I see is when you

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don't know what that next point

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of profitability is going to be.

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You get stuck in a trough.

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Mm-hmm.

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Where

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you are having to make extra

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investments in operating expenses in

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people that you can't pay for yet.

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And you meant to move through that

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in three to six months, and all of a

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sudden it becomes two years and the

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debt becomes unsustainable, right?

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Mm-hmm.

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And then you get really stuck.

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Mm-hmm.

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So you have to have a plan for

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what is the next milestone.

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What do we need to do to get there

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what's gonna be the uncomfortable stuff

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that we have to do in the meantime?

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Mm-hmm.

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Um, to get us through this phase.

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then you can be there and say, I like this

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size of business and this is great for me.

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I love it here.

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Or you can be like.

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That wasn't so hard.

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I think I wanna go for the next one,

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and then we need to look ahead and

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say, not just based on the revenue

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number that you wanna be at, but what

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is the right size of your business at

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the next iteration where we hire the

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people, we have the profitability, you

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get paid what you wanna get paid, you

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keep the culture that you wanna keep.

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What's that next point?

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Okay, let's move toward that.

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What's, how long is this

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next phase gonna take?

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But I think it's the

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stepping stone approach.

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Making sure we're just moving

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through an investment phase to a next

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point of sustainable profitability.

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That's the way that we scale

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a self-funded business.

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You know, I think that even with the

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expert, certainly one who's relatively

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new in their business and they're not

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even thinking in terms of profitability,

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they're thinking in terms of matching

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their old salary and I'll say, you know.

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When I first started, being self-employed,

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I was not thinking about profitability.

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It was literally like, how much

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do I need to make to pay my bills?

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It was not about, you know,

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what does it really cost to me

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to generate this much revenue?

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and so there is a like kind of a,

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a foundational misunderstanding

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or lack of understanding, I think

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for some, experts about just that,

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about profits as opposed to just.

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Revenue.

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So Yeah.

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Yeah, I think that's a great point.

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There is definitely a transitional moment

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when you're that expert solopreneur.

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Mm-hmm.

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To moving into, I'm going to

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run a scaled business now.

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Mm-hmm.

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And other humans are involved, whether

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they are employees or contractors or

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other businesses that you work with.

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How do I go from how I do it myself?

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Self.

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Mm-hmm.

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And to take most of the money

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and put it in my bank account.

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Right.

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And just be tax smart about that.

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Right.

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And how do I set things up so other

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people can replicate what I do mm-hmm.

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At this level of quality

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that I wanna sustain.

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Mm-hmm.

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Because people still need to,

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you know, still mostly me, right?

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And so how do I bring in the right people

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and then how much is that gonna cost?

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I think that that is a point where.

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We really have to think

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through what you charge.

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Mm-hmm.

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And how many clients you need, or

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how many sales you need, and what

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that next investment is gonna be.

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Because bringing on people is a big leap.

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It is expensive.

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Yes.

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Yes.

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Right.

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They come with a lot of rules.

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I'm in California.

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Ah, yes, you had one part-time employee,

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you better have a retirement plan.

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You better be thinking about

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all of your compliance, right?

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that is that one human being

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for more than 10 hours a week.

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We have to do that.

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So, you know, there are other

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places where it's not that, really

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do have all of these other layers

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of operating and administrative

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responsibility once you start to scale.

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Mm-hmm.

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And do you want your expertise to

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become, I wanna get really good at.

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operating a business.

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Mm-hmm.

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Or I wanna get really good at

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going and finding customers

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and telling them my story

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mm-hmm.

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And aiming my business in that direction.

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And I think that's one of the

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challenges of people get really

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bogged down at that next phase of.

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I don't know how to do any of this stuff.

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Mm-hmm.

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And it's really hard, and I keep

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getting letters and they're scary

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and I don't wanna like, and now I'm

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spending time on, on hold, trying to

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figure out what's going on and like,

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who do I need to solve this problem?

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the sales stop, you stop selling, you

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stop focusing forward and you stop

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innovating and you stop trying stuff.

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that is one of the big pitfalls

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of going from a single expert.

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Into a scaled business setting mm-hmm.

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Is, we rise to the place where the

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administrative stuff overwhelms us.

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Yes.

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And then who do you get

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to help you with that?

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Mm-hmm.

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Right?

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How do you get good at that a lot

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faster.

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Mm-hmm.

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Right.

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Yeah.

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I'm a huge, Proponent of division

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of labor, there's something I

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don't even wanna get good at.

Speaker:

Yes.

Speaker:

Like for me to go from, the, uh, what

Speaker:

is it, the zone of genius, go, yes.

Speaker:

Not even adequate to decent would be

Speaker:

like, that gap is, for some things

Speaker:

is huge for me versus going from

Speaker:

good to great, you know, which is

Speaker:

where I'm trying to spend my time.

Speaker:

So you mentioned, having a

Speaker:

scalable, sustainable business.

Speaker:

And from my perspective, you

Speaker:

can't do that without developing

Speaker:

some intellectual property.

Speaker:

Not necessarily software books or courses,

Speaker:

but you know, making sure we're capturing

Speaker:

our expertise putting it in a form that

Speaker:

it can be replicated by other people.

Speaker:

You know, as founders, we are the most

Speaker:

expensive resource in our business,

Speaker:

so how do we have less expensive

Speaker:

resources deliver some or all of that.

Speaker:

Value to our clients.

Speaker:

And so I get too many questions

Speaker:

about like, I'm worried about people

Speaker:

stealing my intellectual property and.

Speaker:

one of the things that you do

Speaker:

is you have a ask me anything.

Speaker:

Mm-hmm.

Speaker:

Where you let people come and you

Speaker:

give away your, expertise for free.

Speaker:

some people and I do a lot of that

Speaker:

as well, and people are like, why you

Speaker:

give so much away, but where do you see

Speaker:

the benefit of sharing your expertise?

Speaker:

well, most of the things that I know

Speaker:

you will eventually learn, right?

Speaker:

Mm-hmm.

Speaker:

I was a proud business auntie earlier this

Speaker:

year as one of my clients got on stage, in

Speaker:

front of a group of other women and said

Speaker:

things that I know I said to her, mm-hmm.

Speaker:

She said them to these,

Speaker:

bigger group of women.

Speaker:

And I was just like, yes.

Speaker:

Pass on that message.

Speaker:

Mm-hmm.

Speaker:

We all can get better at this.

Speaker:

Mm-hmm.

Speaker:

So I think, I come from a place

Speaker:

where innovation is the ip.

Speaker:

Creating an organization that will be

Speaker:

curious and continue to learn, continue

Speaker:

to try new things continue to really

Speaker:

move ahead to new opportunities and

Speaker:

being smart about what we need to

Speaker:

protect in that and what is protectable,

Speaker:

Because innovation in and

Speaker:

of itself is a discipline.

Speaker:

Mm-hmm.

Speaker:

Is

Speaker:

not protectable.

Speaker:

Right.

Speaker:

The product of your innovation

Speaker:

might be protectable.

Speaker:

The question is like, is it relevant

Speaker:

for a long time, if it takes

Speaker:

several years to get a trademark,

Speaker:

or it takes, utility patent, right?

Speaker:

Mm-hmm.

Speaker:

Is that.

Speaker:

A useful investment for you?

Speaker:

Is that something that's the

Speaker:

product of your innovation mm-hmm.

Speaker:

That you need for a long time?

Speaker:

And

Speaker:

so a lot of what we're doing in

Speaker:

our intellectual property is really

Speaker:

that special sauce of how do we

Speaker:

make our business ours, What are

Speaker:

the operating procedures we follow?

Speaker:

Mm-hmm.

Speaker:

How do we think about who

Speaker:

we bring onto our team?

Speaker:

Other people can't replicate that.

Speaker:

Mm-hmm.

Speaker:

And I think also that

Speaker:

curiosity, did it move forward?

Speaker:

Most organizations are not that.

Speaker:

Mm-hmm.

Speaker:

So you know that aspect of

Speaker:

we will continue to evolve.

Speaker:

Versus, you know, often people

Speaker:

with intellectual property think,

Speaker:

I've got my thing now I'm gonna

Speaker:

milk it for the next 75 years.

Speaker:

And that might be true as you capture some

Speaker:

of these things, put copyright on them.

Speaker:

Mm-hmm.

Speaker:

Absolutely.

Speaker:

There are things that, you know, might

Speaker:

live well beyond you where your heirs

Speaker:

can continue to get money from them.

Speaker:

Mm-hmm.

Speaker:

And understanding what those

Speaker:

things are are really important.

Speaker:

and where those fall in.

Speaker:

But I think sometimes people get.

Speaker:

Too attached to, I protected this

Speaker:

thing so that nobody else can use it.

Speaker:

And it's really the defense of that,

Speaker:

that they haven't thought through.

Speaker:

Mm-hmm.

Speaker:

Like, do you wanna become an organization?

Speaker:

That is defending a copyright

Speaker:

or defending a trademark.

Speaker:

Mm-hmm.

Speaker:

Or do you wanna be this

Speaker:

thing in the world?

Speaker:

Mm-hmm.

Speaker:

so I think that's the kind

Speaker:

of the balance of you have to

Speaker:

understand what intellectual

Speaker:

property will and won't do for you.

Speaker:

Mm-hmm.

Speaker:

I think one of the things that I do with

Speaker:

my clients is we look at insurances.

Speaker:

if intellectual property

Speaker:

is important is mm-hmm.

Speaker:

How do we form a legal

Speaker:

defense fund mm-hmm.

Speaker:

Using

Speaker:

insurance.

Speaker:

That

Speaker:

gives us the right to say, not only are

Speaker:

we gonna write that cease and desist, but

Speaker:

when you think you've, you know, scared us

Speaker:

with a big lawyer, we have a bigger lawyer

Speaker:

and we're gonna write a nastier letter.

Speaker:

' cause we have a legal defense

Speaker:

fund that you didn't know we had.

Speaker:

I went through this with a client

Speaker:

a few years ago where, you know,

Speaker:

there's like a major manufacturer

Speaker:

that thought they would scare her off.

Speaker:

Mm-hmm.

Speaker:

And she.

Speaker:

It was like, I have insurance for this.

Speaker:

Mm-hmm.

Speaker:

I'm getting a good lawyer.

Speaker:

Right.

Speaker:

And went ahead and like, wrote

Speaker:

back the letter and they were

Speaker:

like, oh, oh, she's for real.

Speaker:

Right.

Speaker:

So I think there are things like that not

Speaker:

just the intellectual property, but the

Speaker:

defense of intellectual property mm-hmm.

Speaker:

Yeah.

Speaker:

Is a thing as small business owners, that

Speaker:

there are tools that we can use mm-hmm.

Speaker:

To make us run with

Speaker:

against bigger companies.

Speaker:

And I think that's a big thing

Speaker:

to think about if you are

Speaker:

gonna be an IP driven business.

Speaker:

Yeah.

Speaker:

I love that, and I will, people

Speaker:

probably forget this about me, but

Speaker:

the, my brand name Think Beyond

Speaker:

IP was about kind of not just.

Speaker:

copyrights, trademark patents, it was

Speaker:

about all kind of intellectual capitals

Speaker:

I called it, you know, which it is

Speaker:

called, but which nobody wanted to hear

Speaker:

me talk about, which is yeah, what my

Speaker:

evolution was like, okay, nobody really

Speaker:

wants to talk about intellectual capital.

Speaker:

but it's exactly, of course, I didn't

Speaker:

put it the way you put it, but about.

Speaker:

Culture, innovation, all those things.

Speaker:

Insurance, there's a whole, ecosystem

Speaker:

of how we create a business that,

Speaker:

is differentiated, that people wanna

Speaker:

work in, that clients wanna work with.

Speaker:

It's not just about, what is

Speaker:

filed in a copyright office.

Speaker:

and those things are all.

Speaker:

Absolutely.

Speaker:

So important.

Speaker:

So thank you for putting it that way.

Speaker:

I feel I feel better about,

Speaker:

I'm so glad to hear that.

Speaker:

I feel so much better.

Speaker:

So tell me how, your clients

Speaker:

know, Hey, I need to call Jill.

Speaker:

Like, what's happening

Speaker:

in their businesses?

Speaker:

Yeah.

Speaker:

Yes, yes.

Speaker:

so often with my clients, like you

Speaker:

ask me about like why I do so much

Speaker:

stuff for free and I consider like

Speaker:

I want to be Mackenzie Scott level.

Speaker:

Giving Right.

Speaker:

And not keeping what I have, right?

Speaker:

Mm-hmm.

Speaker:

And I want lots of

Speaker:

people to be successful.

Speaker:

So my business model, what I've

Speaker:

settled on for my own growth

Speaker:

is more of a freemium model.

Speaker:

Mm-hmm.

Speaker:

Lots of people are on my newsletter.

Speaker:

Lots of people come to my free stuff.

Speaker:

We work with 10 or 12 clients a year.

Speaker:

And a lot of those clients

Speaker:

stay on for multiple years.

Speaker:

So really, when it comes to

Speaker:

new clients, we're taking on

Speaker:

four to six new clients a year.

Speaker:

Mm-hmm.

Speaker:

Right?

Speaker:

Mm-hmm.

Speaker:

Until

Speaker:

they phase through and hire,

Speaker:

permanent people mm-hmm.

Speaker:

if they get that big to take these

Speaker:

on permanent jobs, all of mm-hmm.

Speaker:

You know, four or five, six

Speaker:

things we're doing for that.

Speaker:

Mm-hmm.

Speaker:

So I think the point that people end up

Speaker:

calling me is they either say, Hey, I've

Speaker:

been running this business for a while.

Speaker:

I have an idea of like how to take it

Speaker:

to the next level, but I need someone to

Speaker:

help me think through what is that right?

Speaker:

Like what are my options?

Speaker:

How could I do it And then how do

Speaker:

I stay true to me while I do that?

Speaker:

What are the centering principles that

Speaker:

matter that we're building this business

Speaker:

around, what are the forms the business

Speaker:

could take that don't trade off who I am?

Speaker:

What matters to me getting paid, right?

Speaker:

Because none of us can go to zero.

Speaker:

Mm-hmm.

Speaker:

We gotta get paid while

Speaker:

we build these things.

Speaker:

And when I get to the other

Speaker:

side, is it still a business?

Speaker:

I'm gonna be happy running.

Speaker:

is it still a thing?

Speaker:

Does it become somebody else's

Speaker:

thing or is it my thing?

Speaker:

And so I think when you're having

Speaker:

thoughts like that's the moment to

Speaker:

call me as a thought partner and

Speaker:

a strategist of what could it be?

Speaker:

Right.

Speaker:

Let's talk about what it could be.

Speaker:

and that's like kind of bringing in

Speaker:

the structures and, you know, different

Speaker:

capital models and things like that.

Speaker:

And that's where I draw a

Speaker:

lot on my venture background.

Speaker:

Mm-hmm.

Speaker:

And also what I know about

Speaker:

money management of like, how

Speaker:

would we make that happen?

Speaker:

The other piece that

Speaker:

people call me for is.

Speaker:

All I'm doing now is admin, Like I

Speaker:

really wanna get back to, focusing

Speaker:

on the, the growth of my business,

Speaker:

selling things, talking to customers,

Speaker:

running my team, and I'm so bogged down

Speaker:

in all this other stuff and I don't

Speaker:

even know the right questions to ask.

Speaker:

And also.

Speaker:

I know I'm getting these giant tax bills.

Speaker:

I know they're more, I

Speaker:

know I could be smarter.

Speaker:

I know I could give more

Speaker:

benefits to my people.

Speaker:

I tend to work with very generous founders

Speaker:

who do more than the law requires, right?

Speaker:

Mm-hmm.

Speaker:

They wanna share all the

Speaker:

rising tide lifts, all boats.

Speaker:

That's the attitude.

Speaker:

Mm-hmm.

Speaker:

So, how could I do that?

Speaker:

What's good for me and

Speaker:

what's good for them?

Speaker:

So, you know, that's very often of

Speaker:

how do we fix the running it part of

Speaker:

the business so that you are doing

Speaker:

the running it part that you want.

Speaker:

And we take all that stuff that, you

Speaker:

know, when you say something like,

Speaker:

Hey, I'd like to implement this in the

Speaker:

business and I just see 11 to 15 things

Speaker:

we're gonna need to do to do that.

Speaker:

Right?

Speaker:

You don't have to go through the trial

Speaker:

and error of what are those things.

Speaker:

We make a checklist, we step through them,

Speaker:

we prioritize them, and we might, you

Speaker:

know, in many cases, just do them for you.

Speaker:

So I think that part is like an

Speaker:

operating partner, an experienced

Speaker:

operator in so many different

Speaker:

areas of running, small business.

Speaker:

And when I say small, like.

Speaker:

You know, that's up to

Speaker:

like $15 million, right?

Speaker:

I'm just talking about a hundred

Speaker:

thousand dollars businesses here.

Speaker:

There's a wide range of small business.

Speaker:

Mm-hmm.

Speaker:

But I think that's, the point of when

Speaker:

the operating of the business has

Speaker:

gotten overwhelming for you, but it's

Speaker:

still cost prohibitive to bring in a

Speaker:

really experienced operating partner.

Speaker:

That's the other time to call me.

Speaker:

That's fantastic.

Speaker:

So speaking of how you work with

Speaker:

your clients, is there anything

Speaker:

new and exciting coming up in your

Speaker:

business that you'd like to share?

Speaker:

Yes.

Speaker:

I'm really investing in my newsletter

Speaker:

and my community around that.

Speaker:

something that's free.

Speaker:

We have lots of resources, I don't want

Speaker:

anyone to fail in starting a business

Speaker:

because they didn't file a piece of paper.

Speaker:

Or they didn't know they

Speaker:

had a deadline mm-hmm.

Speaker:

Or they got behind on their taxes.

Speaker:

Right.

Speaker:

All of those things that you just don't

Speaker:

know when you first start a business.

Speaker:

Mm-hmm.

Speaker:

So, you know, the newsletter and

Speaker:

the community around that, are free

Speaker:

and it's, you know, just something

Speaker:

that I want as many people as

Speaker:

possible to get to the place where

Speaker:

they could be become my clients.

Speaker:

Right.

Speaker:

Like, that's all.

Speaker:

Mm-hmm.

Speaker:

Uh, so we're really, you know,

Speaker:

focused in on like, what else

Speaker:

can we do for that community?

Speaker:

Of self-funded small business owners

Speaker:

to help them get to that point.

Speaker:

and I think on the other side of the

Speaker:

business, I'm really leaning more into,

Speaker:

some of the wealth management aspects of,

Speaker:

you know, that's kind of a hidden aspect.

Speaker:

I was a registered investment

Speaker:

advisor, for several years.

Speaker:

And so like I've been through all

Speaker:

the training on, personal wealth.

Speaker:

Mm-hmm.

Speaker:

Uh, and that's part of it be coming

Speaker:

from investment being as well.

Speaker:

when you're in a pass through entity,

Speaker:

when you're an S corp. When you're an LLC.

Speaker:

The opportunities of how

Speaker:

to compensate yourself.

Speaker:

Mm-hmm.

Speaker:

And what your world are look very

Speaker:

different than when you have an investor

Speaker:

who said you take a salary mm-hmm.

Speaker:

And you're gonna work

Speaker:

for a long time mm-hmm.

Speaker:

Until you get paid out.

Speaker:

I think the piece of like,

Speaker:

especially in the flux of the current

Speaker:

administration, I. How can we not be

Speaker:

afraid and operate in a smart way?

Speaker:

And that additional piece of,

Speaker:

you know, your responsibilities

Speaker:

as a business owner mm-hmm.

Speaker:

But also your opportunities.

Speaker:

That's a new layer.

Speaker:

I think that's really, more people are

Speaker:

asking about in our operating work.

Speaker:

Ah, well, I will say I'm going

Speaker:

through that right now, so that

Speaker:

is definitely hitting home for me.

Speaker:

So, very interesting.

Speaker:

Thank you for sharing that.

Speaker:

And you answered my last question,

Speaker:

which is first steps for people to get

Speaker:

going on this journey, but signing up

Speaker:

for your newsletter and getting access

Speaker:

to, all of the, generous information

Speaker:

that you share, I think is fantastic.

Speaker:

We'll make sure we have links

Speaker:

to everything in the show notes.

Speaker:

Where else can people find you, Jill?

Speaker:

So my website is the Jill James.

Speaker:

If, you wanna join the newsletter,

Speaker:

it's the jill james.com/newsletter.

Speaker:

I also have a booking link on my website.

Speaker:

I know people are a little hesitant

Speaker:

to use it, but I'll talk to

Speaker:

anybody for 20 minutes and mm-hmm.

Speaker:

And brainstorm with you.

Speaker:

So, you know, feel welcome to use

Speaker:

that if you know you've heard some

Speaker:

things here that you wanna talk about.

Speaker:

I'm on LinkedIn Threads Blue Sky.

Speaker:

Hmm.

Speaker:

And Instagram, as, the Jill James.

Speaker:

Mm-hmm.

Speaker:

the company is, and then my

Speaker:

personal LinkedIn is Jill d James.

Speaker:

I'm curious about your use

Speaker:

of Instagram for what you do.

Speaker:

Like, do you find your

Speaker:

clients there or have?

Speaker:

Do you use Instagram?

Speaker:

Instagram for me is more of

Speaker:

a credibility, uh mm-hmm.

Speaker:

Step, I talk to a lot of people of like.

Speaker:

Various ages.

Speaker:

Mm-hmm.

Speaker:

Right.

Speaker:

And one of their checks for, especially

Speaker:

for some of the more creator driven

Speaker:

businesses that I work with, is

Speaker:

they go to my Instagram page first.

Speaker:

Mm-hmm.

Speaker:

Mm-hmm.

Speaker:

And they wanna see that I'm legit.

Speaker:

Mm-hmm.

Speaker:

And that I've made an effort.

Speaker:

So we don't do a lot of original content.

Speaker:

Like we repurpose a lot of the newsletter

Speaker:

content and just repackage it, with

Speaker:

graphics for Instagram, or I'll make

Speaker:

short videos, or we'll take an a MA clip.

Speaker:

but it is an important.

Speaker:

Credibility.

Speaker:

I treat it like a billboard.

Speaker:

Mm-hmm.

Speaker:

Like it's a live billboard for me.

Speaker:

Mm-hmm.

Speaker:

Of when you pass by.

Speaker:

Is there something useful there

Speaker:

and do you know how to contact me?

Speaker:

So that's really, that's

Speaker:

the role for Instagram.

Speaker:

you're right, it's not driving mm-hmm.

Speaker:

Business directly.

Speaker:

But I do hear a lot of people say,

Speaker:

Hey, you know what, I really, I

Speaker:

found you because you put something

Speaker:

interesting on Instagram and

Speaker:

I wanted know more about that.

Speaker:

Yeah, yeah, yeah.

Speaker:

That is why I haven't used, what could

Speaker:

I do, that would be catchy enough

Speaker:

for Instagram, which I feel like

Speaker:

needs like kind of another level of

Speaker:

creativity than say LinkedIn and so

Speaker:

yeah, I've been thinking about that one.

Speaker:

And then, do you use TikTok or.

Speaker:

I don't use TikTok.

Speaker:

I have all the security concerns about

Speaker:

that and I have from the beginning.

Speaker:

so yes, I've had many people over

Speaker:

the years say, Hey, this is new.

Speaker:

You could be the blank of TikTok.

Speaker:

And I was just, you know,

Speaker:

I've had things like that.

Speaker:

I've, my business has not been

Speaker:

on Facebook and we've been off.

Speaker:

What X since 2017.

Speaker:

Mm-hmm.

Speaker:

Yeah.

Speaker:

And I think this is part of, you

Speaker:

know, my centering principles is if

Speaker:

the only way my business can make it

Speaker:

is by being on platforms that I don't

Speaker:

wanna be on, then I'm okay if I fail.

Speaker:

Hmm.

Speaker:

That's a great way to look at it.

Speaker:

Yeah.

Speaker:

Well, this has been a

Speaker:

wonderful conversation.

Speaker:

Thank you so much, Jill, for generously

Speaker:

sharing your wisdom with the audience.

Speaker:

And, to everyone, please, make

Speaker:

sure you get on Jill's, email

Speaker:

newsletter list and, 'cause.

Speaker:

Of information shared.

Speaker:

And thank you again.

Speaker:

yeah, hopefully we'll do it again soon.

Speaker:

Thank you, Erin.

Speaker:

I would love that.

Speaker:

Thanks for having me.

Speaker:

I.

About the Podcast

Show artwork for Scaling Expertise
Scaling Expertise
Strategies for Exceptional Leaders Driving Sustainable Growth

About your host

Profile picture for Erin Austin

Erin Austin

Meet Erin Austin, a Harvard Law alum with over 25 years of copyright and contracts experience. As the go-to advisor for professionals with corporate clients, Erin empowers entrepreneurs to be their own advocates, standing out for her commitment to transforming expertise into empires through the creation, protection and leveraging of intellectual property assets. Explore her blend of legal expertise and entrepreneurial insight on ThinkBeyondIP.com and the "Hourly to Exit" podcast. Off the clock, you'll find Erin in the great outdoors or connecting with business coaches to elevate 6-figure consultants into 7-figure powerhouses.