Ground Control: Sponsored by RocketDocs

What happens when your company’s second workforce is made of AI agents, and nobody is managing them? In this episode of Ground Control, the RocketDocs podcast, Bryan Jenkins sits down with Ted Wolf, CEO of GuideWise. Ted started his career at IBM, then co-founded a technology consulting business with his brother on $1,000 and grew it to 650 billable employees over 18 years before it was acquired by a publicly traded company. Today he and his son run GuideWise, helping organizations set business objectives, choose the right technology, and get their people to actually adopt it.

Ted opens with a scenario most businesses haven’t considered: an employee who dislikes the company’s approved AI platform finishes a proposal on a personal laptop over the weekend. The work gets done, but in the process they may have broken NDAs, exposed client IP, and created real legal liability. That is ungoverned AI, and Ted argues it is the challenge everyone will be talking about in 2027.

Bryan and Ted dig into AI governance and agent orchestration at scale, why enterprise data and a single source of truth matter more than siloed data and tribal knowledge, how poorly designed agents send token costs through the roof, and why compliance frameworks like SOC 2 are becoming a requirement rather than a nice to have. Ted also explains why defining what an agent should not do is the heart of governance, and why every agent still needs human accountability for accuracy, just like a new employee.

The conversation turns to the human side of AI transformation: the burnout that comes when the pace of change outruns an organization’s ability to adapt, why individuals cannot wait for leadership to teach them AI, and the two skills Ted says everyone needs to build now: managing conflict, starting with yourself, and critical thinking. He walks through GuideWise’s Intelligence Curve and the “leapfrog moment,” when governed, orchestrated agents start compounding intelligence with every proposal and decision, and shares his timeline for 2027 through 2029. Ted also shares real results, including a work in process report cut from two weeks to two minutes and a SOC 2 Type 1 implementation completed in 58 days.

Connect with Ted on LinkedIn, email him at [email protected], or check out his YouTube podcast, Implementers.

Ground Control is brought to you by RocketDocs, the response management platform built for regulated industries.

Most founders are not building a business from day one - they are building a prison. In this episode of Ground Control, the podcast on AI, proposals, and governance sponsored by RocketDocs, host Perry Robinson talks with Peter Boolkah, award-winning business coach, creator of The Hamster Wheel Trap, and author of Your Business Sucks. After 15 years climbing the ladder at McDonald's and more than 50,000 hours coaching business owners, Peter's core lesson is simple: there is no work-life balance, only balance, and it comes from competency and structure. Peter and Perry cover why year five is when founders have the most to lose, what McDonald's systemization teaches about SOPs, how to use ChatGPT or Claude to document how your business runs, why company knowledge matters through turnover, and what Pep Guardiola teaches about building a team. His closing line: the more you learn, the more you earn.

Connect with Peter Boolkah

Work with Peter: https://www.boolkah.com/

LinkedIn: https://www.linkedin.com/in/boolkah/

Get the book (Your Business Sucks): https://shop.boolkah.com/product/your-business-sucks/

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Website: https://rocketdocs.com

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Most organizations are not short on smart people or good ideas. They are short on clarity. In this episode of Ground Control, the podcast on AI, proposals, and governance sponsored by RocketDocs, host Perry Robinson and co-host Bryan talk with Catherine Webb, founder of Nova Grace Advisory and a governance leader who spent decades running PMOs, mergers, regulatory programs, and a multi-million dollar global AI deployment inside top-five financial institutions. The core lesson: a sound strategy still stalls when the execution model underneath it cannot turn that strategy into coordinated decisions. Catherine covers how to separate real governance from bureaucracy, where the truth disappears between project reporting and the executive dashboard, how to define who recommends, who decides, and who can stop the work, why a decision record has to preserve the why and not just the outcome, and who should own AI outcomes and hold the authority to pause. Her closing line: never forget your foundation.

Connect with Catherine Webb

Work with Catherine: https://novagraceadvisory.com

LinkedIn: https://www.linkedin.com/in/catherine-webb-62218b97/

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Apple Podcasts: https://podcasts.apple.com/us/podcast/ground-control-sponsored-by-rocketdocs/id1896052098

Spotify: https://open.spotify.com/show/00xAPsKE61ff5X5YC4ndRA

YouTube: https://www.youtube.com/@rocketdocs6075

All episodes: https://rocketdocs.com/resources/podcast

Find RocketDocs

The response management platform built for regulated industries - trusted since 1994.

Website: https://rocketdocs.com

Book a demo: https://rocketdocs.com/demo

LinkedIn: https://www.linkedin.com/company/rocketdocs

00:00 Introduction and Guest Background

02:06 Experience in Mergers and Project Management

05:53 Digital Transformation and AI Initiatives

08:23 Common Challenges in Complex Projects

10:19 Organizational Clarity and Capacity Issues

11:39 Governance and Decision-Making Processes

13:33 The Role of Dashboards and Information Flow

14:53 Engaging Leaders and Understanding Business Benefits

16:27 Decision Ownership and Record Keeping

18:46 Handling Role Changes and Knowledge Transfer

21:21 Regulatory and Risk Program Insights

22:38 Decision Records and Documentation Importance

23:24 Accountability and Cross-Functional Coordination

25:11 The Role of PMO in Information Management

26:08 Creating Value Through Governance

27:36 AI Deployment and Organizational Readiness

28:27 AI Risks, Controls, and Human Oversight

29:52 Stopping AI Projects and Governance Triggers

31:53 High-Leverage Changes for Leaders

33:13 Contact and Final Thoughts

Daniel Rock did not choose sales. He was an IT manager who realized he liked the business problem more than the technology, phoned his own telecom account manager, and six weeks later was selling IT with no sales experience at all. Twenty years on he is chief revenue officer at Suite Files, and his argument is that curiosity, not polish, is what separates good sellers from replaceable ones. In this episode of Ground Control, the podcast on AI, proposals, and governance sponsored by RocketDocs, hosts Perry Robinson and Bryan Jenkins talk with Daniel about why most reps ask a list of discovery questions and never the question after that, what AI is genuinely good at versus where it quietly invents commitments your product cannot keep, the real cost of stale answer libraries and security questionnaires, and how to write a follow up that is not "just checking in." His line for the whole thing: curiosity is a salesperson's superpower.

Connect with Daniel Rock:

→ Work with Daniel: https://danielrock.co

→ LinkedIn: https://www.linkedin.com/in/danielrock/

Find Ground Control:

→ Apple Podcasts: https://podcasts.apple.com/us/podcast/ground-control-sponsored-by-rocketdocs/id1896052098

→ Spotify: https://open.spotify.com/show/00xAPsKE61ff5X5YC4ndRA

→ YouTube: https://www.youtube.com/@rocketdocs6075

→ All episodes: https://rocketdocs.com/resources/podcast

Find RocketDocs:

The response management platform built for regulated industries - trusted since 1994.

→ Website: https://rocketdocs.com

→ Book a demo: https://rocketdocs.com/demo

→ LinkedIn: https://www.linkedin.com/company/rocketdocs

Most B2B proposals lose before anyone reads a word of the pricing. In this episode of Ground Control, the podcast on AI, proposals, and governance sponsored by RocketDocs, host Perry Robinson talks with Will Leach, best-selling author of Marketing to Mind States and founder and CEO of the Mind State Group. A former military engineer turned behavioral scientist, Will spent 25 years studying why people really buy and the answer is almost never the reason they give you.

The core lesson: 95% of decisions are made below conscious awareness, inside temporary emotional states Will calls mind states. Identify the four factors behind one goals, motivation, regulatory approach, and cognitive biases and you can write a proposal, email, or RFP response that fits how the reader actually decides, instead of competing on features.

Along the way Will covers the PULL framework for qualifying real opportunities, how he uses AI to embed psychological cues in his deliverables, the graphic-novel trick that makes buyers feel like the hero, selling to committees you never meet, and Bevi, his behavioral intelligence system that lets brands ask a virtual customer what it thinks. His closing line: all we did was put science around intuition.

Connect with Will Leach

Work with Will: https://mindstategroup.com/

LinkedIn: https://www.linkedin.com/in/will-leach/

Get the book (Marketing to Mind States): https://a.co/d/0cnopkoY

Find Ground Control

Apple Podcasts: https://podcasts.apple.com/us/podcast/ground-control-sponsored-by-rocketdocs/id1896052098

Spotify: https://open.spotify.com/show/00xAPsKE61ff5X5YC4ndRA

YouTube: https://www.youtube.com/@rocketdocs6075

All episodes: https://rocketdocs.com/resources/podcast

Find RocketDocs

The response management platform built for regulated industries - trusted since 1994.

Website: https://rocketdocs.com

Book a demo: https://rocketdocs.com/demo

LinkedIn: https://www.linkedin.com/company/rocketdocs

An AI assistant that gave itself a phone number, and a startup that let a bot buy a $40,000 Davos delegacy.

Host Perry Robinson and RocketDocs AI practitioner Bryan Jenkins use those stories to show that teams are adopting AI faster than they are governing it. They cover vendor diligence, data sovereignty, and the new Sovrinty partnership. The mantra: policy is a promise, architecture is a guarantee.

Episode Chapters

00:00 Welcome + what's to come

00:25 What today's episode covers

00:58 AI adoption versus AI governance

02:11 The IAPP and EY study: 77% working on it, 57% not in control

03:59 Most people do not know how their AI handles data

04:45 Open-agent tools and losing control of AI

05:39 The assistant that gave itself a phone number

06:50 The startup AI that bought a $40k Davos delegacy

07:51 Marketing security claims versus reality

09:26 When "secure" is just a contract, and terms change

10:44 Read the privacy policy, not the marketing

13:15 You are the data: cheap AI, big deficits, lock-in

14:13 Trusting AI answers you know are wrong

15:35 Prompt injection in resumes and the proposal space

16:29 Both sides use AI: answering and evaluating RFPs

17:26 Asking ChatGPT how to evaluate AI vendors, and itself

19:34 Vendors that deflect the data flow question

20:58 ChatGPT's own no-go indicators

23:33 Why de-identified and aggregated is not enough

24:55 Court cases, legal holds, and "once it is out, it is out"

26:02 Policy is a promise, architecture is a guarantee

26:50 Contract terms flowing down: a financial services example

27:49 The overnight scramble to re-qualify a vendor

28:39 Coming enforcement actions and downstream fines

29:42 Defining data sovereignty

32:29 How little control most people actually have

33:37 Better AI results from controlling what it sees

35:18 Source citations and countering hallucination

36:06 Introducing Sovrinty: keeping knowledge current and approved

39:00 Portability, Glean, and 150 fractured repositories

41:27 Sovrinty versus Snowflake

45:29 Closing checklist: do real diligence, do not just rely on AI

46:40 Invest now in accurate AI sources

47:20 SOC 2 scope: is the AI even covered?

48:51 Ask for a data flow diagram and the vendor's AI contract terms

51:23 Think different: stay skeptical of AI

52:07 Keep your company's unique voice

53:15 Wrap-up and a call for listener stories

Find Ground Control

Apple Podcasts: https://podcasts.apple.com/us/podcast/ground-control-sponsored-by-rocketdocs/id1896052098

Spotify: https://open.spotify.com/show/00xAPsKE61ff5X5YC4ndRA

YouTube: https://www.youtube.com/@rocketdocs6075

All episodes: https://rocketdocs.com/resources/podcast

Find RocketDocs

The response management platform built for regulated industries - trusted since 1994.

Website: https://rocketdocs.com

Book a demo: https://rocketdocs.com/demo

LinkedIn: https://www.linkedin.com/company/rocketdocs

Juliet Fletcher has spent nearly 40 years in proposals and helped her clients win more than $1 billion in awards, but the experience that shaped everything came before she ever wrote one. As an intern for the Florida Division of Cultural Affairs, she reviewed proposals for compliance and sat through panel hearings all the way through award. That reviewer's seat is her secret sauce: design your document so the evaluator can instantly find what they need, because if they have to hunt for it, they start to like you less. She and host Perry Robinson get into her "human discernment enforcer" mindset, why evidence beats AI-generated narrative, why a strong proposal writer is a persuasive communicator rather than a technical writer, and the bid/no-bid discipline that keeps you from chasing what you can't win. Her mantra: persuasive communication is never about you, it is about them - write without fear, edit without mercy.

Episode Chapters
00:00 Introduction to Juliet Fletcher and her expertise
01:13 Juliet's background in proposal review and compliance
03:01 Designing proposals for reviewer ease
06:06 The human discernment enforcer mindset
07:47 The importance of evidence and proof points
11:07 Organizing proposal content as a database
14:35 Using AI tools for proposal drafting
19:00 Persuasive communication and storytelling
23:28 Challenges with AI-generated content
28:02 Engaging SMEs and making them feel valued
33:47 Starting early and learning from past proposals
39:11 Best practices for post-proposal analysis
44:11 Evaluating AI tools and competitive intelligence reports
51:20 Final advice and how to connect with Juliet

Connect with Juliet Fletcher
Work with Juliet: https://writingiseasy.com
LinkedIn: https://www.linkedin.com/in/julietfletcherwritingiseasy/

Find Ground Control
Apple Podcasts: https://podcasts.apple.com/us/podcast/ground-control-sponsored-by-rocketdocs/id1896052098
Spotify: https://open.spotify.com/show/00xAPsKE61ff5X5YC4ndRA
YouTube: https://www.youtube.com/@rocketdocs6075
All episodes: https://rocketdocs.com/resources/podcast

Find RocketDocs
The response management platform built for regulated industries - trusted since 1994.
Website: https://rocketdocs.com
Book a demo: https://rocketdocs.com/demo
LinkedIn: https://www.linkedin.com/company/rocketdocs

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 ([email protected]) 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.