What can a 150-year-old cavalry defeat teach a modern RFP team racing against the clock? More than you'd think.

In this episode of Ground Control, Perry Robinson sits down with David Fivecoat, a West Point graduate, 24-year Army veteran, executive coach, and author of Growing Your Grit, to explore how battlefield decision-making translates into everyday business leadership. David runs immersive leadership programs that take corporate teams to historic battle sites, from Gettysburg to the Battle of the Little Bighorn, where standing on the actual ground makes the lessons stick in a way no conference-room keynote can.

Perry and David dig into Custer's fatal failure to adapt when the Native American coalition changed the rules of engagement, and why that's the perfect metaphor for leaders navigating AI and rapid change today. They unpack John Boyd's OODA loop (observe, orient, decide, act) and why speed and a willingness to update your mental model matter more than ever when time kills deals. David also breaks down how to write a leader's intent that actually aligns an ad-hoc team, the discipline of real goal setting, and why the best leaders never stop studying their craft.

Whether you're formally managing a team or just taking charge of the next big push, this conversation is packed with practical, hard-won ideas you can put to work tomorrow.

Want a copy of David's book, Growing Your Grit? The first 20 listeners to email us (marketing@rocketdocs.com) or repost this episode on LinkedIn and tag @RocketDocs will get one.

Learn more about David at TheFivecoatConsultingGroup.com or connect with him on LinkedIn (David Fivecoat / The Fivecoat Consulting Group).

Chapters

00:00 Introduction to Leadership and Military History
01:39 The Concept of Staff Rides and Leadership Training
04:29 Experiential Learning on Battlefields
07:36 Lessons from the Battle of Gettysburg
10:33 The Battle of Little Bighorn: A Case Study
13:19 Adapting Leadership in Times of Change
16:33 The OODA Loop and Its Application
19:29 Time Management and Decision Making in Leadership
22:32 Crafting Effective Purpose Statements and End States
25:17 Measuring Success in Leadership
27:08 Developing Leadership Skills
32:09 The Importance of Self-Study
33:43 Understanding Grit and Purpose
37:09 Effective Goal Setting
39:52 Writing and Publishing a Book
48:12 Connecting with David Fivecoat

What happens when guardrails aren't enough?

On this episode of Ground Control, host Perry sits down with Dr. Craig Kaplan, cognitive psychologist, AI researcher, and founder of SuperIntelligence.com, for a wide-ranging conversation on why safety has to be built into AI's architecture, not bolted on after the fact.

Craig's path into AI started as an undergraduate studying psychobiology, which led him to Carnegie Mellon, where he worked alongside Nobel laureate Herbert Simon, one of the field's founding figures. From there he founded IQ Company in 1993 and, later, Predict Wall Street, a crowdsourced hedge fund built on a simple but radical bet: that the aggregated opinions of millions of everyday retail investors could outperform the best-funded quant researchers on Wall Street. It worked. The fund ranked in the top 10 of its class before Craig sold the company in 2020, having proven what he calls collective intelligence in the most competitive arena imaginable.

That experience became the foundation for how Craig thinks about AI safety today. He argues that the dominant approach to building large language models, pouring in more data and compute to create ever-larger "black box" systems, is fundamentally the wrong design. Guardrails added after training are a losing game of whack-a-mole: easy to jailbreak, impossible to fully patch. Instead, Craig makes the case for something closer to a democracy than a dictator: architectures built from many smaller, checkable intelligences that create transparency, checks and balances, and distributed power, the same qualities that make human institutions resilient to bad actors.

Perry and Craig also dig into what this means practically for businesses adopting AI: why companies should never rely on a single model for mission-critical decisions, how to make sure a company's own values and ethics get explicitly built into the systems it deploys, and what obligations companies have to be transparent with employees and customers about where their AI comes from and how it's being used. The conversation closes with a rapid-fire round covering Craig's revised AGI timeline, what Herbert Simon might make of his work today, and why Craig believes the data shows humanity's track record is better than the doomer narrative suggests, if we can just get AI to match our values.

Guest: Dr. Craig Kaplan, LinkedIn | SuperIntelligence.com

0:00 Introduction: Meet Dr. Craig Kaplan
0:50 From Psychobiology to AI: Studying Under Nobel Laureate Herbert Simon
3:06 Founding IQ Company in 1993
4:06 The Three Eras of AI: Symbolic, Machine Learning, and Reasoning
7:58 Quantifying the Pace of AI Progress
10:15 Predict Wall Street: Proving Collective Intelligence in the Markets
16:22 Why AI Guardrails Fail: An Ounce of Prevention
23:07 Designing Safer AI: Black Boxes vs. Democratic Architecture
29:13 Sovereign Intelligence and Owning Your Data
34:36 Bounded Rationality and the Case for Mixture of Experts AI
40:53 What Do Companies Owe Users About Their AI?
49:27 Rapid Fire: Predictions, Regrets, and Final Thoughts

What does it mean to be "suffocated by success" and how do you break free? In this episode of Ground Control, Perry Robinson sits down with Jonathan Maddock, a systems engineer turned program manager turned attorney with nearly 30 years inside the Department of Defense. Jonathan brings a rare perspective forged at the intersection of military leadership, government bureaucracy, and commercial enterprise, where competing priorities are the norm and alignment is the mission.

Jonathan shares the thinking behind his book Suffocated by Success, exploring how founders and leaders unknowingly become the bottleneck in their own organizations. Drawing on his engineering and legal backgrounds, he breaks down why every business, no matter the size or industry, is a system of systems, and what happens when leaders fail to treat it that way.

Perry Robinson and Jonathan dig into founder ego, the temptation to jump in and solve every problem, and why the fastest path to sustainable growth often requires slowing down first. Jonathan uses a simple but powerful analogy: letting your kids struggle through the wrong answer on their homework so they actually learn how to find their way back. The same principle applies to building a resilient team and a scalable business.

The conversation also covers the role of AI in managing complex systems, how RocketDocs and businesses like it can benefit from systems thinking, how to distinguish between self-imposed urgency and real constraints, and why patience is not the opposite of speed but the foundation of it.

Jonathan closes with a message that goes beyond business strategy and operational efficiency: a reminder that each of us is our own system of mind, body, and soul, and that mental health awareness, including being kind to yourself, is part of operating at your best.

Chapters:

00:00 Introduction to Jonathan Maddock's Background
05:32 The Concept of Being 'Suffocated by Success'
11:12 Understanding Systems in Business
16:38 The Role of Founders and Ego in Business
22:17 Integrating Engineering and Legal Systems
23:35 Understanding Legal Systems Through Engineering Principles
26:22 Breaking Down Complex Problems into Manageable Components
28:55 The Role of AI in System Management
32:38 Navigating Fragility in Business Systems
35:13 The Importance of Patience in System Development
36:35 Learning Through Challenges: The Founder’s Journey
39:27 Balancing Speed and Systematic Growth
43:35 Mental Health Awareness in System Management

Connect with Jonathan on LinkedIn or visit fortivianstrata.com to learn more about his work and pick up a copy of the book.

Ground Control is sponsored by RocketDocs, the response management platform built for regulated industries and trusted since 1994. RocketDocs helps teams in financial services, healthcare, life sciences, and enterprise tech streamline RFP responses, DDQ automation, security questionnaires, and sales proposals using private AI. RocketDocs is designed to help teams win more business faster without sacrificing compliance or quality. Learn more at rocketdocs.com.

Breaking Into Government Contracts: What You Need to Know Before You Start

Selling to the government sounds like a dream. Steady clients, long-term relationships, and reliable revenue. But the path to becoming a government-approved vendor is anything but simple. In this episode, Bryan and Perry sit down with Lori Crooks, founder and CEO of Cadra, a compliance consulting firm helping small and mid-sized businesses navigate the complex world of government contracting.

Lori breaks down the alphabet soup of compliance frameworks (FedRAMP, GovRAMP, CMMC, NIST) and explains what they actually mean for your business. She shares why starting with compliance early is the single most important thing a company can do, how FedRAMP authorization can open doors far beyond federal agencies, and what continuous monitoring really looks like once you're approved.

Whether you're a small business curious about government contracts or already knee-deep in the process, this conversation is packed with honest, practical guidance on what it takes to get in and stay in the government contracting space.

In this episode:

• The difference between FedRAMP, GovRAMP, and CMMC
• Where to start if you're new to compliance frameworks
• Why policies and procedures matter more than most companies realize
• How AI is reshaping both cybersecurity threats and compliance tools
• The hidden business benefits of compliance beyond winning contracts
  

Connect with Lori: cadra.com | lori.crooks@cadra.com | LinkedIn: Lori Crooks

00:00 Introduction to Government Contracting
02:28 Navigating Compliance Frameworks
05:12 Understanding FedRAMP and GovRAMP
08:02 Starting Your Journey in Government Contracts
10:48 The Importance of Early Engagement
13:31 Maintaining Compliance and Continuous Monitoring
16:10 Automation in Compliance Processes
18:50 Organizing Information for Audits
21:39 Utilizing Tools for Compliance Management
22:55 Navigating Compliance Standards
24:06 Assessing Readiness for Compliance
25:32 The Importance of Comprehensive Policies
27:41 The Role of Documentation in Compliance
29:44 How to Reach Out for Compliance Help
32:06 Understanding the Rewards of Compliance
35:42 The Impact of AI on Compliance Standards
38:36 Future Changes in Compliance Landscape
40:58 Starting with Compliance Early

In this episode of Ground Control, Sr. Director of Customer Success Lindsey Bohlender and Customer Success Associate Mallory Ulrich sit down to tackle one of the biggest challenges facing proposal teams, content managers, and business development professionals today: how do you build a knowledge management system that actually stays current, organized, and valuable over time? Whether you are a brand new RocketDocs customer going through onboarding or a seasoned team looking to level up your content operations, this episode is loaded with practical, real world advice you can start applying immediately.

The conversation kicks off with a deep dive into content ownership and accountability, exploring how organizations of all sizes, from small teams without a dedicated content manager to large enterprises with multiple subject matter experts and compliance stakeholders, can create a culture where everyone takes responsibility for keeping information accurate and up to date. Lindsey and Mallory break down how leadership buy-in is the single most important factor in driving adoption of any new process or content management workflow, and how framing the conversation around efficiency, time savings, and risk reduction is the key to getting executives and team leaders on board.

From there, the episode gets into the nuts and bolts of organizing your knowledge base in a way that mirrors your actual business structure, including how to segment content by department, product line, deal size, and ARR tier so that autofill and automated workflows can do the heavy lifting when deadlines hit. They also cover how to use usage counts, content reporting, and date tracking to identify what is performing, what is stale, and what should be archived so your subject matter experts are not wasting time maintaining records that are never being used in live proposals, RFPs, DDQs, or security questionnaires.

Lindsey and Mallory also discuss the importance of proactive content review cycles, whether that means quarterly audits, annual cleanups during slower business periods, or automated review reminders built directly into your workflow, so your team is never scrambling to get fifty SMEs to review a two hundred question document the week it is due. The episode wraps with a conversation about how reducing that reactive, deadline driven chaos is not just good for efficiency but is also critical for compliance, audit trails, and demonstrating to regulators and clients exactly where your content came from and when it was approved.

If you are in proposal management, sales operations, revenue enablement, legal, compliance, or anywhere in between, this episode will give you a fresh perspective on how to build a knowledge base that your whole team will actually use, trust, and maintain.
00:00 Maximizing Value from Rocket Docs

02:41 Ownership and Responsibility in Content Management

05:38 Utilizing Reporting for Effective Content Management

08:55 Determining Focus Areas for Content Updates

11:22 Organizing Information for New Customers

15:09 Implementing Effective Workflows

18:30 Leadership Buy-In for Process Adoption

RocketDocs CTO Gary Murry joins Perry Robinson and Bryan Jenkins on Ground Control for a conversation that covers a lot of ground. Gary started his career as a mathematician, landed a contract role at Apple in the late eighties, and has spent the decades since working across some of the most interesting corners of Silicon Valley technology. Now he leads engineering at RocketDocs, where his team is navigating one of the most transformative moments in the company's thirty-year history.

In this episode, Gary breaks down the thinking behind RocketDocs' latest product release, including features built around simplifying Excel downloads from web portals, marking questions from inside the Launchpad Word plugin, locking down SharePoint permissions at a more granular level, and automating reminders so that both project contributors and knowledge base owners stay on track without needing to be chased down manually. Each feature traces back to a real pain point Gary's team heard directly from customers, and he explains how they use those conversations to decide what to build, what to generalize, and what to leave out entirely.

Gary also shares a grounded and practical perspective on where AI is today versus where people imagine it to be. He talks through why RocketDocs built on a RAG-based model to reduce hallucinations, why giving the AI permission to not answer a question was one of the most important decisions they made, and where even the most advanced generative models still break down when faced with common sense problems. For anyone working in proposals or adjacent fields, his advice on how to review AI-generated content and where errors tend to sneak in is genuinely useful.

The episode wraps with rapid-fire questions on favorite technologies, what Gary would and would never use general AI tools for, and why his answer to staying relevant in an AI-powered world comes down to one thing: go play with it and see what happens.

00:00 Introduction to Gary Murry and His Background

02:44 Transition from Mathematics to Technology

05:29 Joining Rocket Docs and Embracing Change

08:23 Balancing Work and Personal Interests

11:14 Feature Prioritization and Customer Feedback

14:03 Innovations in Rocket Docs and AI Impact

16:45 Navigating Customer Requests and Simplifying Solutions

20:54 Meaningful Steps in Scrum Development

21:42 The Importance of Tinkering with Technology

23:25 Understanding AI: Current State vs. Science Fiction

25:11 Limitations of AI: Common Sense and Logic

27:20 Navigating AI's Logical Leaps

28:28 Hallucinations in AI Responses

30:26 Keeping Content Healthy with AI

31:30 Future of AI in Content Curation

32:06 Favorite Technologies and Their Applications

33:32 Privacy Concerns with AI

34:37 Challenges in AI Efficiency

35:29 Essential Skills for the Future: Prompt Writing

36:27 The Joy of Tinkering and Learning

In this episode of Ground Control, host Lexi Hotchkin sits down with Perry Robinson and Bryan Jenkins to tackle the most pressing questions hitting proposal and RFP teams right now. How do you keep your brand voice when AI is writing your responses? What happens when buyers start banning public AI tools from the RFP process? And is building your own AI solution actually saving you money, or quietly killing your competitive edge?

The conversation covers retrieval augmented generation (RAG) and why your content library is your biggest differentiator, the rise of new AI driven roles like content strategist and AI library manager, the shadow AI confidentiality risks nobody is talking about yet, and the IKEA vs Meta case study that reframes what smart AI adoption actually looks like. Whether you are a proposal manager, sales leader, procurement professional, or RFP specialist, this episode gives you the frameworks to stay competitive, stay compliant, and sound like yourself, not a robot.

What you will learn in this episode: how to maintain brand voice in AI generated proposals, what RAG technology is and how it works for RFP teams, how to build and manage an AI content library, who should own your AI knowledge base, the real cost of building vs buying AI tools, how to keep subject matter experts engaged in the proposal process, what shadow AI risk means for enterprise sales teams, how AI is changing roles in proposal management and procurement, what the IKEA and Meta approaches to AI workforce strategy can teach your team, and how to write RFP responses that win whether a human or an AI is scoring them.

Topics covered include RFP automation, proposal management software, AI for sales teams, enterprise AI adoption, retrieval augmented generation, content library management, human in the loop AI, AI governance, procurement technology, bid management, shadow AI risk, build vs buy AI, AI workforce strategy, content strategy, and RFP response best practices.

Most proposal professionals focus on answering RFP questions, but Kristina Nolan reveals how mastering the art and science behind proposals can unlock exponential growth for your team. Discover how strategic thinking, building relationships, and understanding the buyer's mindset can transform a standard response into a powerful competitive advantage.

Kristina, Proposal Strategy Manager at the Deals Desk at HubSpot, shares her journey from international relations to proposal mastery. She explains how her background in critical thinking and game theory influences her approach. Kristina uncovers hidden tactics used to influence procurement processes, such as leveraging public information, timing, and relationship-building, even in unpredictable environments. Learn why a proactive, consultative approach often outperforms reactive tactics, especially when resources are limited.

In this episode, you'll learn how to identify signals that indicate whether an opportunity is worth pursuing amidst fierce competition. Discover the secret sauce for evaluating deals based on both data and intuition. Understand why AI isn't just about automation; it’s a tool to ensure compliance and identify gaps early, while still leaving room for the human touch to craft compelling narratives. Explore the importance of understanding industry language and competitor cues to spot influence and avoid misleading AI outputs.

Get practical tips for embedding equity, diversity, and sustainability into your proposal strategy, even when organizational support is limited.Mastering proposal responses is not just a skill; it’s a strategic move to dominate your market.

Whether you're in SaaS, government contracting, or any competitive industry, Kristina’s insights will help you turn proposals from mere checkboxes into door-openers, creating trust, shaping buying decisions, and accelerating growth.This episode is perfect for proposal managers, sales strategists, and business leaders committed to winning smarter, not harder.

If you want your proposal team to deliver more than just answers, if you aim to influence, predict, and win, this episode is your blueprint.