How to Navigate Your Post 40 Pivots, LIVE in Chicago with Pam Sunshine and Jenn Sherman of Sunny and Jenn
Dear FoundHer...Real Founder Stories for Women Small Business Owners
Lindsay Pinchuk
4.9 • 1.1K Ratings
🗓️ 4 February 2025
⏱️ 42 minutes
🧾️ Download transcript
Summary
Sometimes, the best opportunities come out of nowhere—just ask Pam Sunshine and Jenn Sherman!
Lindsay Pinchuk kicks off a live conversation from a sold-out event in Chicago, where she sits down with Sunny and Jenn to talk about unexpected pivots, reinvention, and rolling with life’s surprises. A chance encounter on the street sent these two best friends viral on TikTok, launching them into a new chapter they never saw coming. With no strategy, no grand plan, and no clue what they were doing at first, they figured it out along the way and built something real.
Jenn shares how she went from stay-at-home mom to Peloton instructor, proving that taking one small step can change everything. Pam opens up about stepping into the spotlight after decades behind the scenes and why this new venture feels different—it’s just for her. They also talk about balancing careers, navigating midlife shifts, and why embracing what excites you matters at any age.
The best things often happen when you say yes before you feel ready. This episode is a reminder to embrace change, lean on your support system, and go after what excites you because the right opportunities often show up when you least expect them.
Quotes
- “You have to find something you’re passionate about and that you love that’s going to push you.” (07:49 | Jenn Sherman)
- “You have to dive in and just decide you’re going to figure it out.” (15:36 | Jenn Sherman)
- “We’ve learned that we’re just going with it. And if you don’t feed it, it can’t grow. We definitely have learned that. And sometimes that gets a little tricky.” (16:07 | Pam Sunshine)
- “I’m a big sharer because if I have something good, why wouldn’t I want to share it with people I like? I’m just not a gatekeeper.” (24:12 | Pam Sunshine)
- “When you just can be yourself, it’s very freeing.” (26:17 | Pam Sunshine)
- “You have to first put yourself out there and decide you want to make that change. And don’t wait. You’ve heard it a million times. Just do it.” (34:52 | Jenn Sherman)
Connect with Pam Sunshine and Jenn Sherman:
http://www.instagram.com/sunnyandjenn
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Join the Dear FoundHer... Forum: https://www.dearfoundher.com/dear-foundher-forum
Don't forget to follow Lindsay on Instagram: https://www.instagram.com/lindsaypinchuk
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Transcript
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| 0:00.0 | Hi guys, it's me, Lindsay Pinchuk. Welcome to season four of Deer Fountain. We kicked off last week. |
| 0:06.5 | What started as a podcast here at Deer Founder is now a movement. And I can't wait for you to see what we have in store around here in 2025. |
| 0:14.7 | I'm going to remind you, every decision that we've made here, it's because you've asked us to. |
| 0:20.2 | From our mentorship |
| 0:21.0 | opportunities, our online community, our workshops, our courses, and our live events, which |
| 0:26.0 | brings me to today's episode. Last year, you guys asked me to bring my friends Pam Sunshine and |
| 0:31.4 | Jen Sherman, otherwise known as Sunny and Jen, on the road for a bigger dear founder event. |
| 0:37.1 | And so we hosted a test event here in |
| 0:39.1 | Chicago where I live. And under an hour, we sold out of 150 premium tickets and in less than 10 |
| 0:44.9 | days, the entire 400 seat theater was sold out with the wait list. And many of you asked to hear |
| 0:50.9 | the conversation that took place that night. So today, you can listen in on an edited |
| 0:55.7 | version of what went on on our very first, but definitely not last, Dear Fountain on tour event. |
| 1:02.1 | Which brings me to the last thing that I just said. We have so much more coming your way |
| 1:08.2 | in terms of events and opportunities here at Dear Fountain in 2025. |
| 1:13.4 | From online workshops, which we kicked off last Friday, with incredible women who are |
| 1:18.7 | experts in their field of business, to in person and online networking events to more |
| 1:24.0 | dear Fountain on tour. You're going to want to click the link in our show notes and get on |
| 1:28.5 | our list so that you know when we're coming to a city near you. But for now, I want you to sit back |
| 1:34.3 | relax and take a listen to my live interview with Pam Sunshine and Jen Sherman. I promise you're in |
| 1:40.8 | for a treat. Welcome to Dear Founder, the podcast that pulls back the curtain on what it really takes to build and grow a successful business. |
| 1:51.7 | No gatekeeping, no fluff, just real talk. |
| 1:55.9 | I'm your host, Lindsay Pinchuk, award-winning entrepreneur, founder, and proud member of the 1% of female founders |
... |
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