Ryan Connell | Tradewinds × CDAO
Defense Mavericks
Welcome to Defense Mavericks, the podcast that uncovers the untapped potential of AI within the federal government. Join us as we dive into authentic and disruptive conversations with our nation’s brightest minds, offering a fresh perspective on how to gain an unfair advantage through the adoption of new, emerging technology. Our goal is to equip you with the knowledge, education, and best practices you need to shorten the learning curve toward government transformation. CDAO:https://www.ai.mil/Tradewinds AI:https://www.tradewindai.com/
Author
Ryan Connell | Tradewinds × CDAO
Category
Podcast website
Latest episode
Mar 18, 2025
Where to listen?
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Episodes
Nontraditional Procurement Methods in Defense with Stephanie Wilson 21.03.2024 28:19
Today’s bonus episode features listener favorite and contracting powerhouse, Stephanie Wilson, on the Doing Tech Better in Government podcast. Stephanie chats with host, Brian Fox, about her experience with non-traditional procurement methods, combating legacy tech, and getting familiar with the unfamiliar. From AI in procurement to culture change within the DoD, Stephanie discusses the challenges...
Overcoming Bureaucracy in Defense Innovation with Jon Gruen 19.03.2024 29:32
This week, Bonnie is joined by Jon Gruen, CEO of Fortem Technologies and former Navy SEAL, to discuss counter-drone strategies and the challenges of fostering innovation in the defense space. Jon shares his insights on the intricacies of operating in the DoD, the capital-intensive nature of defense technology development, and the importance of education and partnerships in driving innovation withi...
Accelerating AI Adoption with Ramsay Brown 12.03.2024 38:17
This week, Bonnie sits down with Ramsay Brown, CEO of Mission Control AI, at DoD Advantage 2024 to talk about how to keep up with the rapid advancements in AI. Ramsay dives into the impact of AI on industries and personal lives, the looming need for responsible AI governance, and the challenges that organizations face when adopting these technologies. He also shares concrete strategies for maintai...
How Tradewinds is Shaping the Future of Defense Contracting with Bonnie Evangelista 05.03.2024 36:32
This week, our very own Bonnie Evangelista explores the intricacies of AI literacy within the defense sector in this special recast of her presentation at the AI Literacy Conference. Get an in-depth look at how evolving contracting mechanisms like BAAs and CSOs are reshaping the way the military engages with cutting-edge AI technologies, and learn how Tradewinds is revolutionizing contract acquisi...
Instilling AI Readiness Across Your Teams with Capt. Jonathan Haase 27.02.2024 30:24
This week, Bonnie is joined by Captain Jonathan Haase, program manager at PMS 408 in NAVSEA, to talk about the importance of AI readiness in the defense industry. Jon shares his insights on how teams can use AI to enhance work processes, facilitate more meaningful face-to-face interactions, and build stronger team relationships. He teaches us to embrace the power of tech to create a human-forward...
Building a Strong Data Ecosystem with Shubhi Mishra 20.02.2024 31:47
This week, Bonnie is joined by Shubhi Mishra, founder and CEO of Raft, to talk about the importance of building strong data ecosystems in the DoD. She shares her insights on prioritizing users versus buyers, taking an unstructured approach to data intake, and why defense tech startups need to rethink the “valley of death” in order to survive it. Tune in for a fresh take on how to approach data eng...
Empowering Soldier Innovation in the Digital Age with LTG Chris Donahue 13.02.2024 28:24
This week, Bonnie is joined by none other than Lieutenant General Chris Donahue, Commander of the XVIII Airborne Corps, to discuss innovation, AI ethics, and leadership in military operations. He shares his insights on empowering soldiers through collective experimentation, bridging generational tech gaps, and developing and sustaining AI-driven systems. Tune in for an inspiring conversation on th...
The Evolution of Defense Tech with Ben Van Roo 06.02.2024 31:28
This week, Bonnie is joined by Ben Van Roo, CEO and co-founder of Yurts AI, to discuss the rapid evolution of defense tech in the last decade. He shares his insights on the dynamic interplay between defense initiatives and the commercial tech landscape, the pitfalls of dual-use companies, and the fine line between oversaturation and innovation in AI. Tune in for a timely conversation on the curren...
Creating a Culture of Trust and Transparency (Bonnie’s Interview on Instill Culture Lab) 30.01.2024 30:01
This week, Bonnie Evangelista joins Dan Kasper on the Instill Culture Lab video series to dive into the concept of culture and building high-performance teams. With Dan's expertise from his Navy Special Operations days and Bonnie’s experience leading teams in the DoD, they peel back the layers on the emotional impact of leadership, the significance of soft skills, and the transformative approa...
How to Increase Experimentation in the DoD with Victor “SALSA” Lopez 23.01.2024 34:53
This week, Bonnie is joined by Major Victor “SALSA” Lopez, Chief of Autonomy Operations for AFWERX, to discuss how to push past bureaucracy to enable rapid experimentation in the DoD. He shares his insights on leading through innovation, creating a team culture built on psychological safety, speeding up software implementation, and cutting through contracting red tape. Tune in for an in-depth expl...
Balancing AI Automation, Privacy, and Federal Compliance with Igor Jablokov 16.01.2024 34:39
This week, Bonnie sits down with Igor Jablokov, CEO and founder of Pryon, to discuss the balancing act that AI-driven companies currently face when it comes to automation, privacy, and federal compliance. Igor breaks down the President’s recent Executive Order on AI safety as well as how to approach AI risk management, build trust through attribution, and promote responsible AI. Tune in to hear ho...
Navigating Defense Contract Pricing with Ryan Connell 09.01.2024 34:06
This week, Bonnie is joined by Ryan Connell from the Defense Contract Management Agency, to dissect the nuanced world of pricing for government contracts in his personal capacity. From Other Transaction (OT) pricing strategies to understanding the critical balance between cost and value, Ryan dives into the evolving landscape of defense procurement and pricing intelligence. Tune in for a mastercla...
Bridging the Human-Tech Divide with Alexis Bonnell 02.01.2024 36:06
This week, Bonnie is joined by a true powerhouse of tech and humanity – Alexis Bonnell, CIO and Director of Digital Capabilities Directorate of the Air Force Research Laboratory. With a rich background rfrom war zones to Silicon Valley, Alexis unpacks the challenges and opportunities of being at the forefront of change. She shares her insights on using time as a weapon, empowering curiosity within...
Breaking Down SBIR & STTR Programs with Kristina Botelho 26.12.2023 35:24
This week, Bonnie is joined by Kristina Botelho, an esteemed contracting and agreements officer for the Air Force, to discuss the ins and outs of SBIR and STTR programs. With nearly 15 years as a contracting officer, Kristina has become a trailblazing figure known for challenging norms and injecting fresh perspectives into contracting approaches. Kristina dives into the challenges of scaling solut...
Minimizing Red Tape Fatigue (Bonnie’s Interview on All Quiet on the Second Front) 21.12.2023 20:43
In this bonus episode, Bonnie Evangelista joins Tyler Sweatt on the All Quiet on the Second Front podcast to discuss how Tradewinds and the CDAO are transforming conventional procurement models and streamlining the dealmaking process to minimize red tape fatigue. Bonnie dives into the vision behind the game-changing Tradewinds Solutions Marketplace and explores the challenges and hopes for the fut...
Revolutionizing Cyber Defense Strategies with Mike Weigand 19.12.2023 33:18
This week, Bonnie Evangelista dives into the cutting-edge world of defense cybersecurity with co-founder and Chief Growth Officer of Shift5, Mike Weigand. As a former army officer turned cybersecurity pioneer, Mike has taken the helm at Shift5 to revolutionize real-time cyber monitoring solutions across various fleets, including manned aircraft and combat vehicles. Mike shares his keen insights on...
Implementing Digital Twins Across the DoD with John Wargo & Jason Robinson 12.12.2023 35:07
This week, Bonnie Evangelista is joined by John Wargo, CTO, and Jason Robinson, Solutions Architect, from Beast Code for a deep dive into the world of digital twins, cybersecurity, and the unique challenges of innovating within the Department of Defense. John and Jason break down the challenges and successes in pushing the envelope within the DoD, offering insights into adopting agile principles f...
Accelerating and Scaling Defense Acquisition with Sharothi Pikar 05.12.2023 43:15
This week, defense acquisition powerhouse Sharothi Pikar joins Bonnie Evangelista for a deep dive into the world of defense acquisition. As the Deputy CDAO for Acquisition at the Chief Digital and Artificial Intelligence Office, Sharothi brings a wealth of knowledge from her origins as an army civilian computer engineer to her pivotal role at Cyber Command. She discusses the cultural and organizat...
Mastering the DoD Procurement Maze with Cody James 28.11.2023 29:43
This week, Bonnie is joined by Cody James, founder of Open X, a startup ushering in a new era of industrial training. A robotics programmer turned successful entrepreneur, Cody is here to share his journey navigating the intricacies of the DoD and his determination to provide a high-tech training resource to the military world. We also dive into how he won a whopping 27 Phase III SBIRs! Tune in to...
How to Become a Procurement Champion with Will Roberts 21.11.2023 41:20
This week, Bonnie sits down with Will Roberts, Director of Emerging Technologies at ASI Government and former Acquisition Lead of CDAO, to talk about what it takes to become a procurement champion. Will shares a fun yet educational approach to decodifying the contracting space and how acquisition professionals can make “mundane tasks marvelous." Tune in for his insights on the future of contr...
Breaking Ground in the Defense Industry with Alex Wulff, Ben Harpe, and Isaac Struhl 14.11.2023 40:36
Today, Bonnie Evangelista sits down with the founders of Distributed Spectrum, Alex Wulff, Ben Harpe, and Isaac Struhl, to dive into their defense tech startup journey. They share their insights on developing a product for end users, the challenges of navigating defense contracts, and the importance of networking and seeking guidance from experienced founders. Tune in to learn from a group of youn...
Using AI to Enhance Mission Effectiveness with Alex Miller 07.11.2023 36:00
This week, Bonnie sits down with Alex Miller, Senior Science and Technology Advisor for the Army Chief of Staff, for a deep dive into data architecture, AI implementation, and the ever-evolving landscape of technology in the military. Alex shares his insights on the concept of data meshes, bridging the gap between tactical and strategic operations, and the need for continuous transformation. Tune...
Scaling Technology Adoption with Mike Pansky 31.10.2023 31:47
Mike Pansky, Chief Product Officer at IntelliBridge, sits down with Bonnie Evangelista this week to talk about how to keep up with and scale emerging technology. Mike shares his own journey navigating the challenging landscape of piloting, prototyping, and contracting new technology at scale in the DoD. Tune in to learn all about tangible strategies and tactics for incentivizing systems integrator...
Streamlining Government Contracting (Bonnie’s Interview on Closing the Loop Podcast) 26.10.2023 35:19
In this bonus episode, Bonnie Evangelista discusses the inefficiencies in government contracting and how we can leverage the power of AI and LLMs to reduce workflows from 3 months to 30 minutes. She shares insights on defining requirements, using the Tradewinds Solutions Marketplace, and getting clear on your value proposition. Tune in to this special crossover episode with Andrew Camel, VP of Ope...
Incentivizing Change in the DoD with Lt. Gen. (ret.) Jack Shanahan 24.10.2023 37:43
This week, retired Lieutenant General Jack Shanahan, the first director of the Joint Artificial Intelligence Center, joins Bonnie Evangelista to discuss the beginnings and momentum of the JAIC. They explore the challenges and hard work that paved the way for opportunities in AI and acquisition within the Department of Defense and the importance of building relationships, taking risks, replicating...
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