Lindsay's Own Real Founder Story on Managing Teams, Scaling Challenges & Knowing When to Pivot
Dear FoundHer...Real Founder Stories for Women Small Business Owners
Lindsay Pinchuk
4.9 • 1.1K Ratings
🗓️ 10 March 2026
⏱️ 16 minutes
🧾️ Download transcript
Summary
In this episode, host and Founder of Dear FoundHer..., Lindsay Pinchuk, gets real with you about a bump in the road, one of the more relatable real founder stories she's lived through: losing a key team member right when you need them most.
Lindsay spent three months onboarding and investing in her new VA, only to receive an email saying she was done with no notice, no transition. As someone who is actively managing rapid growth and navigating the scaling challenges that come with running a small business solo, this hit hard. And she wants to talk about it, because she knows so many of you are in the same boat when it comes to managing teams and finding the right support.
Here’s what we cover in this episode:
• The full story: What happened with the VA and what it really means to leave a small business owner without notice
• Why managing teams as a solopreneur is one of the hardest parts of scaling challenges no one warns you about
• What’s changing on the podcast this month (and why it’s actually a good thing)
• Lindsay's 5-tip framework for pivoting with purpose when your plan suddenly changes
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Transcript
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| 0:00.0 | Welcome back to Dear Founder. I'm Lindsay Pinchuk, your host. I am so glad that you're here today because I have some things I want to share with you. And if you've been following along for any amount of time, you know that I am always very transparent with you as my community as I build my business right alongside yours. And that is not changing today. In fact, it's kind of the whole point of today's episode. |
| 0:21.2 | Here's what we're covering. I'm going to share with you a bump in the road that happened in my |
| 0:25.6 | business recently. I'm going to let you know what that means for me and our podcast this month. |
| 0:31.3 | And then I'm going to give you my actual framework for how to make a pivot in your own business |
| 0:36.8 | with purpose, not panic. So if you're |
| 0:39.6 | in a season where the plan has changed and you're figuring out what's next, this one's for you. |
| 0:45.1 | Let's get into it. Welcome to Dear Founder. I'm Lindsay Pinchuk, founder, acquired entrepreneur, |
| 0:52.3 | and part of the less than 1% of female founders who |
| 0:55.6 | have led a company through acquisition. I built my first business from just $500 to seven figures |
| 1:01.4 | without a marketing budget, simply using community, smart publicity, partnerships, and clear messaging. |
| 1:07.7 | Now, I host this show for women Over 40 stepping into their next chapter, |
| 1:12.2 | whether that's launching, pivoting, or scaling. Each week, you'll hear real founder's stories |
| 1:17.2 | about growing an audience, getting press, leading teams, navigating, scaling challenges, |
| 1:23.3 | and becoming more visible in the right ways. No fluff, no gatekeeping, just what works. |
| 1:29.1 | Around here, we build businesses that actually work with strategy, visibility, and each other. |
| 1:36.9 | So I first want to share with you the bump in the road. |
| 1:39.7 | I want to share with you what happened. |
| 1:41.6 | You may not know, but I hired a virtual assistant in November. And I went, |
| 1:46.4 | I went through an agency and I had some really great interviews. They put some really great women in |
| 1:51.0 | front of me. And I really liked two of the candidates based on the background of one of them, |
| 1:56.5 | a very specific background, I made an offer to her. And I actually chose the one with the higher hourly rate. |
| 2:03.3 | That's how much I liked her. |
... |
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