The Heart & Hustle Podcast

Episode 469: Lindsey's Entrepreneurial Journey

Release Date: January 27, 2026
Hosts: Evie McLeod & Lindsey Roman

Episode Overview

In this episode, Lindsey Roman takes center stage to share the intricate and inspiring path of her entrepreneurial journey—from her artistic upbringing and initial photography hustle to co-founding The Heart University and building multiple successful businesses. Lindsey opens up about pivoting her career, navigating big life transitions, downshifting to balance motherhood and business, and the lessons learned through both intentional and accidental business moves. Throughout, Evie jumps in with questions, humor, and encouragement, making the episode both practical and heartwarming for creative entrepreneurs at all stages.

Key Discussion Points & Insights

1. Early Influences & The Unexpected Entrepreneur Start

• Lindsey grew up in a family with entrepreneurial roots, though at the time she didn’t recognize it as such. Her mom’s impressive Mary Kay sales career (including “winning a car,” [05:16]) instilled early marketing and sales skills, even as Lindsey initially dismissed the idea of business.
• Her original ambition was to become an actress, leading her to double major in film and theater in college.
• After graduating, an “aha!” moment with her camera—realizing the potential beyond using automatic settings—kicked off her love for photography ([08:59]).

2. Becoming a Photographer: From Hobby to Hustle

• Lindsey's church community provided early opportunities to photograph families, seniors, and church events.
• She realized her passion for evoking emotion through art applied just as much to photography as to acting.
• A pivotal step: investing in education early via a Hillary Rushford Instagram course, which catalyzed both her craft and her online presence ([12:57]).

Quote:

“Even as I was simultaneously growing my photography business, I also kinda knew… there is a clear shift if you scroll back into the depths of 2015… there is some sort of curation happening. Wasn’t good curation, but it was a shift.” – Lindsey, [12:57]

3. The Power of Saying Yes & Expansion Beyond Kansas

• Lindsey’s drive led her to seek out work outside her home state, hustling for opportunities nationwide, even traveling for jobs if clients covered her travel.
• Early destination shoots (e.g., Northern California) expanded her portfolio (“We’re not in Kansas anymore,” [13:42]).

4. Personal Life & Business: Marriage, Military, and Mobility

• Lindsey juggled business growth while her husband Andrew was finishing college, then joined the Coast Guard, which led to a huge move to Hawaii ([15:23]).
• The Hawaii move—originally second choice after Oregon—unexpectedly became the launchpad for Lindsey’s wedding photography brand, leveraging the island’s appeal as a destination market ([20:16]).

5. Mentorship & The Jump to Education

• In Hawaii, Lindsey’s visibility and success led to her first photography mentoring requests. She reflects on how “being just two steps ahead” can be enough to guide others ([22:48]).
• This first mentor session was a lightbulb moment, seeding her path toward education and ultimately co-founding The Heart University with Evie.

6. The Birth and Boom of The Heart University

• Evie and Lindsey hosted their first photography workshop in April 2018, which sold out immediately ([26:17]).
• Rapid workshop sellouts, a growing waitlist, and community demand led to expanding into online courses, digital resources, and podcasting.

Quote:

“At the time, we were like… we could literally do this forever and still not even make a dent in that waitlist. Like, there’s clearly demand here.” – Lindsey, [29:26]

7. Scaling, Motherhood, and Shifting Priorities

• The business saw major growth between 2018 and 2019, but motherhood (welcoming daughter Eloise in 2019) brought a necessary downshift ([32:10]).
• Lindsey openly shares the realities of associating out wedding shoots, the impact of a new baby on business capacity, and evolving her priorities.

8. The COVID-19 Pivot and Business Diversification

• The pandemic forced The Heart University to cancel live events and shift further online, launching a digital shop and expanding product offerings ([34:03]).
• Inspired by the company’s capital and success, Lindsey and Andrew began investing in real estate—renovating and flipping houses unintentionally, learning hard lessons about asset vs. liability along the way ([36:00]).

9. From Real Estate to ‘Silent Businesses’

• The couple parlayed real estate returns into new ventures, including buying and starting a “silent,” brick-and-mortar business in Florida with employees and business partners ([51:22]).
• Seller-financing a land sale led to another investment round and the acquisition of a second brick-and-mortar location.

Quote:

“It wasn’t a smart, intentional business choice at the time, but… favor of God and some ignorance.” – Lindsey, [45:44]

10. Downshifting the Heart & Rediscovering Creative Joy

• By 2023-2024, Lindsey and Evie intentionally downshifted The Heart, pulling back on live events, launches, and large-scale initiatives to focus on what was life-giving and sustainable ([56:56]).
• This allowed Lindsey to return more deeply to wedding photography, as well as to family priorities and homeschooling.

Quote:

“Putting [photography] down not fully, but like nearly… CEO in the heart… you lost a little bit of, like, the art and, like, creativity. That doesn’t get to come out as much when you’re just doing, like, launches.” – Lindsey, [58:38]

11. Memberships, Mom Life, & Multipreneurship

• Lindsey launched “Insiders,” a monthly membership for women blending education, coaching, motherhood, book clubs, and community ([59:15]).
• She highlights the challenge and privilege of building an untraditional family business—where she and Andrew both “do both”: working and parenting together.
• At the time of recording, Lindsey is pregnant again, and balancing multiple businesses with faith, flexibility, and joy ([63:11]).

Notable Quotes & Memorable Moments

• On early dreams versus reality:

  “I was always like, ew, entrepreneurship, no… I think I viewed… oh, that’s, like, starting a corporation.” – Lindsey, [05:44]

• On leveraging art for connection:

  “At the core of it, I loved creating art that elicited emotion in people… that can obviously go towards acting, but it can also go towards photography very well.” – Lindsey, [09:00]

• On life’s unexpected pivots:

  “My life would be a million percent different if this was our path… But we didn’t get our first pick, we got our second pick, which was Hawaii, and thus changed our lives.” – Lindsey, [19:28]

• On diversifying and expanding as an entrepreneur:

  “We could literally do this forever and still not even make a dent in that wait list. There’s clearly demand here.” – Lindsey, [29:26]

• On making business moves (and mistakes):

  “It was probably a liability that God blessed you with an asset at the end for at least the first couple…” – Evie, [62:25]

• On lessons learned:

  “We didn’t blow the money. We didn’t take it and just, like, completely waste it. It was like half liability, half asset.” – Lindsey, [62:10]

• On embracing multi-passionate identity:

  “I went through like an identity crisis in there… Am I a photographer? Am I a business coach? Am I a mom influencer? What am I? I was all of them…” – Lindsey, [57:28]

Timestamps for Key Segments

| Segment | Timestamp | |---------------------------------------------------|------------| | Introduction & Format | 00:00 - 04:45 | | Lindsey’s Family & Early Business Attitudes | 04:45 - 07:25 | | Acting Aspirations, Photography Beginnings | 07:25 - 12:57 | | Growing Photography & First Moves Outside Kansas | 12:57 - 16:08 | | Marriage, Military, Moving to Hawaii | 15:22 - 20:13 | | Mentorship & Coaching | 21:31 - 22:48 | | The Heart University: Workshops & Online Courses | 23:44 - 34:03 | | The heart: Growth, Motherhood, COVID Shifts | 34:03 - 36:00 | | Real Estate Adventures | 36:00 - 47:21 | | Move to Florida, Silent Businesses | 47:21 - 51:22 | | Downshifting the Heart, Rediscovering Creativity | 56:52 - 58:38 | | Launching Insiders Membership, Current Priorities | 59:15 - 63:11 |

Lessons, Themes & Final Reflection

• Embrace the roundabout path: Lindsey highlights how each life decision—intended or otherwise—contributed to her skillset and opened new opportunities.
• Invest early in education and mentorship: Consistent willingness to learn and share led to exponential growth in both influence and earnings.
• Don’t fear the pivot: Lindsey narrates several points of necessary shift—toward family, toward new businesses, and toward rest.
• Balance is individual and ever-evolving: The journey underlines the importance of defining success by your own values, and being flexible as life changes.

Closing Words:

“We’re both learning and growing in the process… In no way is this the end of her journey. She will continue more. It’s the beginning.” – Evie, [62:56]
“Hopefully, this was entertaining… a good updated version of where we’ve been since our baby photography journeys.” – Lindsey, [64:23]

For Listeners

If you loved this honest and thorough peek behind Lindsey’s entrepreneurial curtain, or have questions about business pivots, real estate, education, or mompreneur life, both hosts encourage you to DM them on Instagram!