2025 Group Coaching

Business agility encompasses a wide range of activities, all designed to make your company more effective, delight customers, create a great place to work, and make it sustainable. In 2025, I’m putting together a “mastermind” group of 8-10 executives to focus on three main issues:

1. Increase decision quality - a single better decision can make or save millions of dollars

2. Build “pull” systems like Kanban

3. Build a culture of incremental improvement every day

Monthly meeting: We will meet once a month for 90 minutes to work through my curriculum and discuss decisions people need to make. Topics include:

Worldview exercises
Complex adaptive systems
Ecosystems
Statistical literacy
Decisionmaking under uncertainty
Guestimating
Expected value
Track your decisions
Bayesian reasoning
The 70 percent failure rule
Mechanism design
Pareto distributions
Why board meetings are ineffective and how to fix them
The role of luck in business
The halo effect
Internal prediction markets
Automating workflows
Thinking in bets
Playing eight-ball vs playing nine-ball
Mean reversion
When to double down and when to quit
Doing experiments
Bayesian calibration
Spreadsheet checkup
Never go with your gut
Overconfidence
Overprecision
Foxes and hedgehogs
Cognitive diversity
Dynamic portfolio management
One more time, how do you motivate employees?
Psychographic tests
When to sell a business
Dashboards and data
Convexity
Measuring demand signals
Amazon’s decision framework
The Net Promoter Score and other myths
Marketing automation
Kanban!
Extreme value
Perspective taking
Tactical emphathy
Ready, fire, aim - speed is the new business weapon
Cynefin and other uncertainty frameworks
Metadata and supply vs pull chain
Atomic habits
System 1 and system 2
Portfolio optimization
Beyond budgeting
How to measure anything
Decision frameworks
Heuristics
Cost/benefit vs the precautionary principle
Flat management structures
More Kanban!
Decision tool training
Case studies
Acquisitions

One-on-one meetings: Each month, you’ll get two hours with me to dig into your issues and work through them. In this capacity, I function as a coach for you and your team. You’re welcome to include me in meetings or bring your team or board members to our meetings.

Ad-hoc meetings: Each month, if you have a particular decision to make, you’ll call a meeting, showing your decision framework, along with a date, time, and zoom link. Some number of us will show up to the meeting and give you feedback and have a discussion. Then there’s a silent vote, and you’ll hear from people why they voted the way they did. You can use that as guidance for your decision.

Special guests: Occasionally, I’ll invite a special guest to come speak to us and have a conversation. These will take place roughly two weeks opposite the main monthly meeting.

Decisions are where all the leverage is. My goal is to make these meetings a very good use of your time and pay off in millions of dollars saved or made. You can learn more about pull systems and Kaizen on my home page.

Schedule

I’ll start working with clients in early January, 2025. Our first group meeting will take place near end of January or early February, depending on time zones and schedules. You need to be able to give as much as you get. Schedule a conversation with me to see if you would be a good fit for this group.

Frequently asked questions

What, exactly, do I get?
You get a monthly 90-minute group meeting, two extra hours of consultation, access to the online platform, and ability to ask the group for a vote on a big decision. All the meetings will be recorded and available on the platform, so you can watch or rewatch them any time.

How much does it cost?
The program starts with three months for $8,000. There is no initiation fee. After three months, you can pay $3,000 per month or you can pay $8,000 per quarter.

What is the group decision part?
If you have an important decision to make, contact me and I’ll set it up so you can get it out to the group for feedback.

Will you have guest speakers?
Once in a while, I plan to bring people in from the decision-science community and other places. They may be academic researchers or CEOs of companies or authors. There might be 2-3 of these in a year.

Is there any kind of guarantee?
If you’re not getting your money’s worth, just drop out and don’t pay. However, the course is not designed to be profitable for you on a month-to-month basis. You should be able to look back at the end of the year and see that the course saved or made you several times what you paid. If I can save you from making one big mistake per year or grabbing one unseen opportunity, it will more than pay for itself. So give it at least six months before you decide.

What if I can’t make a meeting?
All meetings are recorded and will be on the private platform, so you can watch or rewatch any of them any time. You’re also more than welcome to send someone you trust in your place.

What about those two extra hours per month?
They are for you to use as you see fit. Often, you’ll want to implement something we talked about, like a prediction market or Kanban or another system. I give you those two hours for follow-up coaching. Can be with your team rather than you personally. These are coaching hours only, I won’t have any deliverables. It’s my goal to give you the right frameworks and help you find the right resources to execute something we discuss in our meetings.

How long does the group last?
In theory, it could run for years. I won’t run out of provocative, innovative materials to present and work on. In practice, I expect people to go for one year and then come back for a second year. Beyond that, we can see what the group wants.

What about consulting?
I do consulting as well. Consulting is where I have deliverables. We can discuss it according to your needs.

What’s this I hear about a trip to Africa?
It’s true! In 2025, I’m taking a select group of clients and their families to East Africa to climb Mt Kilimanjaro and go on safari. This is meant to be hard. It will bind you to your family members and to the group, because we’ll have a lot of preparation to do. Yes, I have done this before.

If I’m willing to pay, will you accept me in the group?
No, you have to qualify and be a good fit for the group. Be sure to book a call and talk with me so we can see whether we’re a fit for each other.

Is there a maximum in the group?
Yes, 12 is the maximum. I’m generally shooting for 8-10 but may extend if I see more people who add value. I won’t accept direct competitors.

About me

I’m David Siegel. I’m a lifelong entrepreneur. I got a math degree from the University of Colorado and a Master’s degree in computer science from Stanford. The only company I’ve ever gotten a paycheck from (other than those I started myself) was Pixar — I was one of the first people hired in 1986. In 1993, I started one of the first web-design and strategy firms in San Francisco and sold it to KPMG in 1999. I’ve been a high-level management & strategy consultant to companies like Sony, Hewlett Packard, Amazon, Office Depot, Lucent, CSC, Intel, NASA, and many start-ups. I’ve started a dozen small companies and had a few good exits. I’ve created some products you see around you every day and are probably on the computer or printer you have in your office. I’ve written five books about the Web and business, four of which have been bestsellers. I’ve given over 200 professional speeches, many of them keynotes at tech or business conferences around the world, many of them for $60,000. I’ve done consulting to $30,000 per day. I’ve been consulting, writing, and talking about "customer led" companies for 15 years. I’ve been published in Forbes.com, The Harvard Business Review, and profiled in Fast Company. I’m a graduate of the Harvard Business School course “Making corporate boards better.” In 2016, I was a candidate to be the next dean of Stanford Business School. After that, I became a leader in the crypto movement. I’ve been to 100 countries and have been an African safari guide. You can learn more on my LinkedIn page. 

The Infinite Game of Life is my new coaching company. I help people with longevity and business. I’m passionate about applying evidence-based methods to change the status quo. I don’t think we should accept the norm, I think we should exceed it personally and in our companies.