Brian Anderson joined me on the show, and we explored what it takes to lead an organization through a shift as big as AI, and why that kind of leadership has to start with the leader going first.
Brian is the CEO and co-founder of Augusto Digital, where he helps organizations harness AI, custom software, and rapid innovation to drive real business outcomes. He has spent over two decades building software, products, and teams, and has guided Augusto through a full pivot toward applied AI.
In our conversation, Brian was candid about the fear and uncertainty of changing direction, the decision to go all in on AI before his team was ready and what it meant to lead by example by doing the work himself first. Brian is honest about the flip side of moving forward, that not everyone comes along for the journey, including good people he valued.
We also got into something I keep coming back to. Brian made Augusto the first client of its own services, applying the same AI systems and processes internally before ever selling them to clients. His point was that it is a lot easier to sell something you have already lived with and have your own results to point to.
This was something deeper than a conversation about AI. It surfaced that change happens when the leader is willing to go first, sit in the discomfort of being ahead of the team and let the work make the case.
Worth your time if you can see where your company needs to go but your team isn’t quite ready to follow.
About Brian Anderson:
Brian Anderson is the CEO and co-founder of Augusto Digital, where he helps organizations harness artificial intelligence, custom software, and rapid innovation to drive ROI-driven business outcomes. With over two decades of experience in software, product development, and entrepreneurship, Brian leads Augusto in guiding clients across industries through complex digital transformation and product development initiatives. His current focus is Augusto's AI Solutions practice, where he works directly with leadership teams to identify low-friction, high-ROI use cases through AI Accelerator Workshops. Guided by Augusto's Digital Pace Framework, Rumble to Quick Wins to Accelerate, he helps clients unlock momentum and clarity by delivering value early and often. Before founding Augusto in 2016, Brian built and led software practices at OST and NuSoft Solutions and launched several SaaS ventures, including Tourneytopia, PayIt2, and TallySheet.
🌐 To learn more about Augusto, head over to: https://augusto.digital
About the Host:
David Kent is the host of The Lead Smarter Podcast, where he has honest, grounded conversations with leaders shaping the future of work, leadership, and organizational growth.
👀 Watch the full episode here: https://youtu.be/gya-Qgx0dzY
🔗 Follow David on LinkedIn: https://www.linkedin.com/in/david-james-kent/
- (00:00) - - Welcome to Lead Smarter Podcast
(00:26) - - Introduction to Brian Anderson(01:57) - - Brian's Entry into Entrepreneurship(02:33) - - Getting Fired and Its Impact(03:48) - - Transitioning to Full-Time Entrepreneurship(05:06) - - The Journey of Becoming a Leader(08:03) - - Creating an Entrepreneurial Culture(09:08) - - Evolving Company Mission(10:42) - - Balancing Vision and Operations(12:17) - - Managing Team Engagement(14:13) - - Navigating AI Landscape(16:05) - - Embracing AI in Business(18:00) - - Applying AI to Own Services(19:57) - - Change Management in AI Adoption(22:37) - - Addressing Client Change Management(27:09) - - Importance of Focused Quick Wins(30:57) - - Leveraging Client Engagement Models(35:02) - - Surprising Outcomes from Rumble(39:19) - - Sources of Information for AI(40:11) - - Personal Development and Learning(41:02) - - Advice to Younger Self(42:07) - - How to Connect with Augusto Digital