94. Innovating the VA Industry: A Thought Leader Chat with Tom & Anna Rogers on Tech, Events & Scaling episode artwork

EPISODE · Aug 6, 2025 · 32 MIN

94. Innovating the VA Industry: A Thought Leader Chat with Tom & Anna Rogers on Tech, Events & Scaling

from Booked Out with Bre · host Bre Cain | Virtual Assistant Wealth Coach

In this episode of Booked Out with Bre, I'm SO excited to bring you a special conversation I had with my friends Anna and Tom Rogers! This chat was pure fire. We brought together three minds passionate about disrupting our industries and thinking bigger. Tom is the head of HeyClients, a software shaking up the coaching market, so it was incredible to sit down and talk about what it truly means to be an innovator. Here’s what I dive into with Anna and Tom: My journey from starting as a virtual assistant to building a 7-figure business, an agency, and now, tech! How I identified major gaps in the VA industry and why I decided to be the one to fill them (hello, "Tinder for VAs" and the industry's first live conference!). The real challenges and mindset required to build a tech platform when you're not a "techy" person. Why now is the perfect time for coaches, VAs, and course creators to innovate beyond their traditional offers. The power of having the audacity to just go for it, even when you don't have all the answers. How I (and they) balance running multiple successful businesses without burnout (hint: it's about team, energetics, and a CEO mindset). Why seeing business as a playground and enjoying the game is key to long term success. If you're a virtual assistant who knows you're meant for more, or an entrepreneur with big ideas, this conversation will give you the permission and inspiration to think bigger, find the gaps in your own market, and go build something truly disruptive! Episode Outline: Introduction: A Special Conversation with Innovators Anna & Tom Rogers (01:28) Bre's Journey: From Virtual Assistant to 7-Figure Business & Industry Leader (03:15) Identifying Gaps in the VA Market: Creating the "Tinder for VAs" Tech Platform (05:11) Creating the Industry's First In Person Virtual Assistant Conference (05:30) Tom's Journey: Seeing a Tech Gap in the Coaching Market with Hey Clients (07:02) The Audacity to Innovate: Challenges of Building a Tech Platform Without a Tech Background (08:22) Why Now is the Time for Virtual Assistants & Coaches to Innovate Their Offers (11:35) The Importance of Building a Sellable Company & Serving the Entire Industry (12:37) The Power of Going For It & Figuring It Out Along the Way (13:19) Finding Your Next Big Idea by Solving Problems in the Marketplace (16:27) The Beta Model: Getting Paid to Create Your Offer Alongside Your Clients (17:41) How to Juggle and Balance Running Multiple Businesses (18:32) The CEO Mindset: Team, Energetics, and Unemotional Leadership (19:09) The Playground Mentality: Seeing Business as a Fun Game (20:47) The Importance of Team & VAs for Scaling and Creating Freedom (23:17) How Taking Time Off Fuels Creativity and Bigger Ideas (24:00) Where to Find Bre, the VA Leadership Academy, and VA Fest (30:33) Closing Remarks (31:32)   Ways to Work with Me: Follow Me on Instagram https://www.instagram.com/heyitsbrecain/ Mom X VA Free Facebook Community https://www.facebook.com/groups/momxva Access My "You're Hired!" VA Portfolio Kit: https://thecaincollective.thrivecart.com/vaportfoliokit/ Apply for the VA Leadership Academy: https://www.breannacain.com/applyvaleadershipacademy/   Connect With Anna and Tom: https://www.instagram.com/heyannarogers https://heyclients.io/   If you enjoyed this episode, I would love it so much if you left a rating and review! This helps us reach more women looking to become a virtual assistant, book out their business, and scale beyond their wildest dreams.

In this episode of Booked Out with Bre, I'm SO excited to bring you a special conversation I had with my friends Anna and Tom Rogers! This chat was pure fire. We brought together three minds passionate about disrupting our industries and thinking bigger. Tom is the head of HeyClients, a software shaking up the coaching market, so it was incredible to sit down and talk about what it truly means to be an innovator. Here’s what I dive into with Anna and Tom: My journey from starting as a virtual assistant to building a 7-figure business, an agency, and now, tech! How I identified major gaps in the VA industry and why I decided to be the one to fill them (hello, "Tinder for VAs" and the industry's first live conference!). The real challenges and mindset required to build a tech platform when you're not a "techy" person. Why now is the perfect time for coaches, VAs, and course creators to innovate beyond their traditional offers. The power of having the audacity to just go for it, even when you don't have all the answers. How I (and they) balance running multiple successful businesses without burnout (hint: it's about team, energetics, and a CEO mindset). Why seeing business as a playground and enjoying the game is key to long term success. If you're a virtual assistant who knows you're meant for more, or an entrepreneur with big ideas, this conversation will give you the permission and inspiration to think bigger, find the gaps in your own market, and go build something truly disruptive! Episode Outline: Introduction: A Special Conversation with Innovators Anna & Tom Rogers (01:28) Bre's Journey: From Virtual Assistant to 7-Figure Business & Industry Leader (03:15) Identifying Gaps in the VA Market: Creating the "Tinder for VAs" Tech Platform (05:11) Creating the Industry's First In Person Virtual Assistant Conference (05:30) Tom's Journey: Seeing a Tech Gap in the Coaching Market with Hey Clients (07:02) The Audacity to Innovate: Challenges of Building a Tech Platform Without a Tech Background (08:22) Why Now is the Time for Virtual Assistants & Coaches to Innovate Their Offers (11:35) The Importance of Building a Sellable Company & Serving the Entire Industry (12:37) The Power of Going For It & Figuring It Out Along the Way (13:19) Finding Your Next Big Idea by Solving Problems in the Marketplace (16:27) The Beta Model: Getting Paid to Create Your Offer Alongside Your Clients (17:41) How to Juggle and Balance Running Multiple Businesses (18:32) The CEO Mindset: Team, Energetics, and Unemotional Leadership (19:09) The Playground Mentality: Seeing Business as a Fun Game (20:47) The Importance of Team & VAs for Scaling and Creating Freedom (23:17) How Taking Time Off Fuels Creativity and Bigger Ideas (24:00) Where to Find Bre, the VA Leadership Academy, and VA Fest (30:33) Closing Remarks (31:32)   Ways to Work with Me:Follow Me on Instagramhttps://www.instagram.com/heyitsbrecain/ Mom X VA Free Facebook Communityhttps://www.facebook.com/groups/momxva Access My "You're Hired!" VA Portfolio Kit:https://thecaincollective.thrivecart.com/vaportfoliokit/ Apply for the VA Leadership Academy:https://www.breannacain.com/applyvaleadershipacademy/   Connect With Anna and Tom: https://www.instagram.com/heyannarogers https://heyclients.io/   If you enjoyed this episode, I would love it so much if you left a rating and review! This helps us reach more women looking to become a virtual assistant, book out their business, and scale beyond their wildest dreams.

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94. Innovating the VA Industry: A Thought Leader Chat with Tom & Anna Rogers on Tech, Events & Scaling

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This episode was published on August 6, 2025.

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In this episode of Booked Out with Bre, I'm SO excited to bring you a special conversation I had with my friends Anna and Tom Rogers! This chat was pure fire. We brought together three minds passionate about disrupting our industries and thinking...

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