Derek Fredrickson left Wall Street in 2008 to run operations for his wife's coaching company, which she describes as having been built on toothpicks and band aids. Sixteen years later he runs The COO Solution, putting fractional COOs inside founder led companies between seven figures and twenty million.

His rule for all of it: you can't scale complexity, but you can scale simplicity. The work is making a business process driven instead of people driven, so the founder can stop white knuckling the day to day and move from the operator seat into the owner seat.

He is also living it himself. He runs every sales call for his own company from France, into a US market, and he knows exactly when that turns him into the bottleneck.

## In this episode

- Why he reads every business in the same order: marketing, sales, operations, then finance

- Where the fractional model fits, and why it spreads too thin above twenty million

- Done for you, then done with you, then done by the team, so the COO never holds the keys

- Drive by delegation, and the questions that make a founder sell themselves on their own idea

- What AI is actually doing for his clients right now: filling in the weekly scorecard nobody wanted to update

- Fixing the problem versus solving the issue that caused it

- Who should not hire a fractional COO, including the owner who could not picture it working remotely

- His ten year, three year, one year plan, and handing off his own sales seat

## Timestamps

00:00 A show for founders who are done being the bottleneck

01:03 Leaving Wall Street in 2008 for his wife's business

02:02 Toothpicks and band aids

03:22 Where fractional fits, seven figures to twenty million

05:15 Marketing, sales, operations, finance, in that order

07:30 You can't scale complexity

08:29 Process driven, not people driven

10:35 Three things on the menu

12:15 Where the founder still sits in the business

14:58 Letting go of the sales seat, including his own

16:58 Founders love the hunt and skip the fishing

18:28 Does the system survive after the COO leaves

20:46 Done for you, done with you, done by the team

23:23 Drive by delegation

24:35 Make the founder sell themselves on the idea

27:22 AI starts with the use case

28:52 The scorecard AI fills in for you

31:26 A dashboard nobody can hide from

32:42 Fix the problem or solve the issue behind it

33:40 Who should not hire a fractional COO

36:01 The owner who could not picture a remote COO

37:38 What is next for The COO Solution

39:28 Where to find Derek

## About Derek Fredrickson

Derek Fredrickson is the founder and CEO of The COO Solution, which places fractional COOs with founder led companies. He spent sixteen years as a second in command, first scaling his wife's business coaching company past seven figures, then as a fractional COO for other growing companies. He hosts The COO Solution Podcast.

Website and podcast: https://thecoosolution.com

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

Listen: https://feeds.transistor.fm/the-operating-system-show

Be a guest: https://crm.frontrangesystems.com/discovery

David Salerno built Solpak into one of Canada's most recognized packaging companies. Six hundred food sector clients across the country, on a team of sixteen people.

He did not get there by being efficient after the fact. He decided early that headcount was a vanity metric and ran the business that way for twenty years. Zapier for a decade, now Claude. The current policy at Solpak is that nobody gets hired unless the leadership team can make a business case for the hire over automating the work.

The moment it became visible to him was a banker sitting across from him for two hours. Numbers growing, obvious activity everywhere, and in two hours the phone never rang and nobody came to the door. The banker could not explain it. David could not either, until he tried, and what came out of that is the Sherpa Method he now coaches other owners through.

## In this episode

- Why he treated headcount as a vanity metric for twenty years, and what that bought him

- The banker who sat in his office for two hours and could not explain the quiet

- Three challenges, three steps each, and the twenty seven questions behind the Sherpa Method

- Why he thinks owners have a clarity problem rather than an effort problem

- Giving a single number to a single person, and the prefab roof problem that dissolved once someone owned it

- The hiring standard at Solpak: no new hire without a business case against automating the work

- Where AI does not belong, and the call he made to a friend's AI receptionist trying to trick it

- The retreat where a team member asked to stop answering the phone, and what it revealed

- Who should not try to build a self managed business

## Timestamps

00:00 A show for founders who are done being the bottleneck

01:04 Six hundred clients on a team of sixteen

01:30 Why he treated headcount as a vanity metric

02:05 The frameworks that hold the ratio together

02:56 Ten years of Zapier, and what comes next

03:39 The phase where David was the company

04:19 What he took from corporate, and what he refused to rebuild

05:23 The banker who could not explain the quiet office

06:40 Growth, sustainability, and everything after

07:27 What makes a discipline stick when a framework does not

08:00 Give the number to a person and watch what happens

09:12 The prefab roof, the five whys, and a problem that dissolved

10:55 Ninety seven percent would recommend, and the alignment behind it

12:48 The failure point he sees coaching owners

13:06 Founders do not have an effort problem

14:05 Three challenges, three steps, twenty seven questions

15:00 The mindset shift nobody gets to skip

15:55 Build the business as the product

16:30 Claude at Solpak, and no hire without a business case

18:03 The four zones of AI

19:35 Calling a friend's AI receptionist to try to trick it

22:23 The retreat where a team member asked to stop taking calls

23:37 Who should not build a self managed business

25:09 Buy Back Your Time, and the thousand dollar hour

25:54 Who the Sherpa Method is actually for

27:02 What is next for Solpak and Entrepreneur Sherpa

28:01 Where to find David

## About David Salerno

David Salerno founded Solpak, a Quebec based packaging company serving hundreds of food sector clients across Canada, and now works with it as a mentor and guide after selling part of the business to two partners. He wrote Built for Freedom and coaches owners through Entrepreneur Sherpa, built on three pillars, grow, sustain and serve. He is Vice Chairman of the Montreal Economic Institute.

Website and free first chapter: https://davidsalerno.com

Entrepreneur Sherpa: https://entrepreneursherpa.co

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

---

The Operating System Show is for founders who are done being the bottleneck in their own business. If you want to be a guest: https://crm.frontrangesystems.com/discovery

Every founder Kati Peterman meets says a version of the same sentence. I'm just not there yet.

Not there yet for a COO. Not there yet for a real operator. And she has come to believe that sentence almost never means what it sounds like it means. It is rarely about the money. It is that a visionary founder cannot picture what that person would actually do all day, so a big salary looks like a bet on a job description they cannot see.

Her answer is to go find the money first. Outstanding collections, billables, how clients pay and when, merchant services. Unglamorous operational leakage sitting there in almost every company. Fix that in the first weeks and the fractional executive has paid for herself, and the founder stops arguing about whether operations deserves funding.

## In this episode

- What fractional actually means now that the word has gone hot, and what it buys a company not ready for a full time hire

- I'm just not there yet, and why that sentence is usually about understanding rather than budget

- The quick win that funds the role, starting with money the business has already earned and not collected

- A better question than calling a founder a control freak: where does my founder have fear right now

- Placing the right person versus installing the system, and why the operator has to actually enjoy the work

- Education as the thing that makes a system stick after the operator leaves

- Where she refuses to let AI go, including refunds and cancellations, and why the sales conversation is burning leads

- Teams running at 120 to 140% capacity, and what it takes to get back to 70

- Who should not hire a fractional executive

## Timestamps

00:00 A show for founders who are done being the bottleneck

01:10 What fractional actually means, and why the word got hot

03:11 The first COO offer, and the gap she kept seeing

05:04 I'm just not there yet, and what founders really mean by it

08:05 Outstanding collections, billables, and money already on the table

09:10 Founders get a bad rap as control freaks

09:54 The better question: where does my founder have fear right now

14:41 Why the operator has to actually enjoy the work

16:59 Education is true empowerment, and what makes a system stick

23:12 Teams at 120 to 140% capacity, and getting back to 70

24:35 Zero AI in refunds and cancellations

26:08 The thing that is not up for debate: response time

28:50 Who should not hire a fractional executive

30:01 Why franchisee owners became the favorite client

31:40 Where to find Kati

## About Kati Peterman

Kati Peterman came up as a chief of staff and integrator inside seven and eight figure companies, then founded FRX, a national bench of fractional executives placed into small and mid sized businesses. She is also COO of Empire Operating System.

FRX: https://yourfrx.com

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

If your team is at 140% and hiring is not on the table, that is the conversation: https://crm.frontrangesystems.com/discovery

JL Heather has a name for the thing that kills a good idea before anyone notices it died.

He calls it can't culture. Not a person saying no, a system saying it for them. Twelve approvals that take six months. A budget objection, a pay grade objection, a resourcing objection, all of them sounding perfectly reasonable on the way out of someone's mouth. Nobody ever makes the decision to kill the project. It just never survives the trip.

Underneath it is omission bias. Put your name on a ten million dollar bet and the downside is career limiting. Say nothing and your name is on nothing, even when a competitor ships the same idea three months later and makes a fortune. Speaking up costs about twice what staying quiet costs, so people stay quiet, and it feels prudent the whole time.

## In this episode

- Getting a room full of executives to commit to one thing, and why scheduling is the first real obstacle

- Compressing what normally takes three to eighteen months into a five day design sprint

- Building runs at light speed now, learning did not keep up, and that gap is where the risk lives

- The three ways a project dies, ranked from best to worst

- Can't culture, and why it is human nature rather than bad people

- Omission bias, demonstrated live on Matt with a ten million dollar hypothetical

- Ask AI for an Italian plumber and you get Mario, why models pull everything back to the middle

- Where AI genuinely earns its place, and the one job it should never be given

- Four to five people, one room, three months, and failure criteria that count as a win

## Timestamps

00:00 A show about removing the bottleneck in your business

01:04 Getting executives to commit to one thing

03:37 Three to eighteen months compressed into five days

04:56 What kills a project that never ships

06:38 The worst case, nobody realizes what happened

08:54 Is can't culture bad, or just human

09:00 Omission bias, and the CEO of MattDixon.com

10:12 Saying no puts your name on nothing

13:34 Ask AI for an Italian plumber and you get Mario

14:33 Where AI earns its place

17:47 What AI is not, and it is not an innovator

23:26 What happens when the quarter goes sideways

25:19 Hit your failure criteria and you have succeeded

26:36 The tipping point that means you need outside eyes

29:36 Where to find JL

## About JL Heather

JL Heather is managing partner and principal executive coach at Centered, where the Breakthrough Lab method takes teams from a North Star sprint through design sprints and into three to six months of coaching on the thing that actually ships. Twenty years inside organizations, working mostly in the digital space. He is writing a book on can't culture and hosts the Breakthrough Innovation podcast.

Centered: https://centered.work

JL's site: https://jlheather.com

If ideas keep dying in your company and nobody can point at who killed them, that is the conversation: https://crm.frontrangesystems.com/discovery

Steve Schroeder has spent almost twenty years finding the delays nobody can see.

He calls it the invisible factory. In a plant you can walk the line and watch the widgets pile up at the slow station. In a digital company the same pile ups exist, they are just invisible, sitting in approval queues and handoffs nobody has ever drawn on a wall. His first value stream mapping event ran inside a large telecom during a stalled Agile transformation. They mapped the billing department onto three walls of stickies and cut lead time on new features by 73%. The executive who walked the walls at the end had no idea any of it was happening inside his own company.

## In this episode

- Why a company doing all the right frameworks can still be stuck, and what the framework cannot reach

- The invisible factory, and why digital work hides its own bottlenecks

- Three walls of stickies, a stunned executive, and a 73% cut in lead time

- What changes when AI joins value stream mapping, including rerunning twelve year old data and finding half a dozen more improvements

- Why a company full of individual AI agents can still be slow end to end

- The two roles that decide whether any of it survives: the value stream sponsor and the value stream manager

- What separates the companies that compound from the ones whose map goes in a drawer

- Utilization is the wrong scoreboard, and Messi walks most of the game

## Timestamps

00:00 A show for founders who are done being the bottleneck

01:07 What a framework cannot fix in a stuck company

02:28 A three year Agile transformation that was not working

04:59 Three walls of stickies and a 73% cut in lead time

07:12 What AI adds to value stream mapping

10:09 Why a company full of agents can still be slow

12:24 Flow Killers and Flow Intelligence, who each book is for

17:57 The moment a client's business actually changes

20:58 What survives ninety days and what goes in a drawer

24:08 The sponsor and the value stream manager

29:32 Your developers are 99% utilized and it means nothing

31:00 Who he helps, and the industry he refuses to touch

35:51 Where to find Steve

## About Steve

Steve Schroeder is the founder of EliteFlow Consulting and Solara Analytics. He pioneered digital value stream mapping, bringing a discipline built for factory floors into software organizations where the work is invisible. He wrote Flow Killers, which catalogs the fifty most common things that quietly slow a technology organization, and Flow Intelligence, on marrying value stream mapping to AI.

EliteFlow Consulting: https://eliteflowconsulting.com

Solara Analytics: https://solaraanalytics.ai

If your own business has a handoff you could not draw on a wall if someone asked, that is the conversation: https://crm.frontrangesystems.com/discovery

A tracking system did exactly what it was built to do. It showed one senior engineer closing seventy percent fewer tickets than everyone around him, and the CEO put him on the list of people to cut. Alisa Reznik made him go have the conversation first. The engineer was spending his days unblocking the rest of the team, which is why their numbers looked so good and his looked so bad.

Alisa spent nearly two decades managing engineers, worked with more than fifty tech companies, and ran operations as a COO across offices in three countries before leaving to build her own practice, Leadify. She uses AI all day and she is clear about where it does not belong.

## In this episode

The one category of work she refuses to automate, and the rule she uses to decide.

The ticket dashboard that recommended firing the most valuable person on the team.

Why "what is the best AI tool for my business" is the wrong question, and what to ask instead.

The CTO who prepared for a hard feedback conversation, then sent the notes over Slack.

Ten hours a week, and the ordinary CEO work that gets those hours back.

Her test for anything you are thinking of handing over: how big is the mistake you can afford.

The Friday deployment that wiped a client's CRM on Monday morning.

What young founders get wrong when they treat Claude as the person who knows.

## Timestamps

00:00 What this show is, and today's guest

01:10 Why she picked "do not delegate everything to AI"

01:57 Fifty plus tech companies, and the thing that breaks the same way everywhere

04:03 Remote versus onsite, and how she runs engineering teams either way

05:41 The first process she refuses to fully automate

07:42 The tracking system that flagged the wrong engineer for cuts

10:46 AI does not save you, it amplifies what is already there

11:02 "I feel redundant, AI can do what I do"

12:48 The wrong question every engineer is asking right now

15:48 Where AI actually worked, and the ten hours a week it gave back

19:24 Moving faster versus avoiding a hard call

20:08 A better question than "what tool should I buy"

22:36 What young founders are still missing

25:10 The feedback conversation that got sent over Slack

29:00 The four zones, and where AI belongs in each

30:05 The rule: how big is the error you can afford

32:44 The Friday deploy that erased a client's data

36:30 Fixing the system and the person running it

37:36 Where to find Alisa

## About Alisa Reznik

Fractional COO and executive advisor, and the founder of Leadify. Nearly twenty years managing engineers, more than fifty tech companies, and operations across three countries. She mentors at Founder Institute and writes about operations and leadership every week.

Find Alisa on LinkedIn.

Listen: https://feeds.transistor.fm/the-operating-system-show

Be a guest: https://crm.frontrangesystems.com/discovery

Timothy Bramlett bootstrapped an AI receptionist by sitting in a dental office day after day and cloning the tool they already hated paying for. He walked away from HP and Capital One, learned the hard way that building first is the wrong order, and now runs Zinng, an agent that answers the calls a small business misses.

He also tells the story of one after hours call that changed how he thinks about what an agent can handle.

## In this episode

- Why building the product first is the wrong order, and what he does instead

- How to start when you cannot find anyone to talk to: clone an existing tool and niche down

- Narrow and deep versus wide and shallow, and why complexity kills small products

- Why 85% of calls to a small business never needed a person

- Speed to lead in a dental office, and what happens after four rings

- The internal tooling he built with Claude Code, and why his engineers still do not trust AI

- How AI moved the bottleneck from writing code to testing it

- Running several agents at once, and where that breaks down

- Why "good enough" beats a better sounding voice

- Telling every caller it is AI, up front, on purpose

- The after hours call he says changed his mind about what an agent can handle

## Timestamps

00:00 Who Timothy is

01:23 Why he was never any good at being an employee

02:50 The first thing he built, and why it went nowhere

03:42 "That is absolutely not my philosophy"

05:39 Build the channel before you build the product

07:45 When you cannot talk to customers, clone and niche down

10:26 Narrow and deep versus wide and shallow

12:34 Why 85% of small business calls do not need a human

14:34 What it is actually worth to the owner

15:31 Speed to lead, and the four ring handoff

17:30 The internal tooling he built with Claude Code

17:59 Why his engineers use AI and still do not trust it

19:20 AI moved the bottleneck from writing to testing

21:00 The anti AI crowd and who gets left behind

22:04 Can you hand AI a whole job yet

28:00 Running several agents at once

29:14 Local models as the backup plan

31:23 What is next for Zinng

32:26 Why good enough beats better sounding

33:38 Tell them it is AI, up front

35:00 The after hours call that changed his mind

36:31 Where to find Timothy

## About Timothy

Timothy Bramlett is a software engineer turned bootstrapped founder. He spent years at HP and Capital One before leaving to build his own products. He co-founded Stammer, a white label AI platform for agencies, and now builds Zinng, an AI phone agent that answers every call a business misses, flags the emergencies, and works around the clock.

Zinng: https://zinng.ai

Instagram: https://www.instagram.com/timothybramlett/

Stammer: https://stammer.ai

Listen: https://feeds.transistor.fm/the-operating-system-show

Be a guest: https://crm.frontrangesystems.com/discovery

Gwen Taniguchi is a Certified Exit Planning Advisor and partner at Peek Advisory. Her diagnostic tool is one nobody talks about: the low grade irritation inside a team. "Why do I always have to fix this?" is not venting, it is a map of where the business depends on one person. Revenue hides operational dysfunction, and Gwen follows the irritation to find it.

## In this episode

* Why exit planning is really about optionality: sell, hire a CEO, or step up to founder, your choice

* The quarter test: surviving two weeks without the owner proves nothing

* How founder dependency starts on purpose and grows insidiously

* Why SOPs alone fail when one person holds the tribal knowledge

* Delegating ownership instead of tasks, and what "done right" has to mean

* Where AI belongs in operations and accounting, and where it never should go

* What buyers actually pay a higher multiple for in diligence

## Timestamps

00:31 Who Gwen is and what exit planning really means

02:42 Irritation as operational data

05:43 The quarter test, what exit ready operations look like

07:35 How founder dependency starts

11:41 The collections story and exception culture

13:49 Gwen's three part approach: leadership, ownership, execution

14:51 Tools: ClickUp and AI agents

16:40 Should AI replace whole departments

20:58 Delegating ownership, not tasks

25:17 What buyers pay a higher multiple for

26:34 When to start exit planning

27:48 What is next at Peek Advisory

## Find Gwen

Peek Advisory: https://www.peekadvisory.com

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

## The Operating System Show

Listen: https://feeds.transistor.fm/the-operating-system-show

Be a guest: https://crm.frontrangesystems.com/discovery

Peter Boolkah spent fifteen years inside McDonald's, which is about the most ruthlessly systematized business on the planet, and then spent twenty one years coaching owners out of the trap he watched them build. His line, and the title of his book, is that if the business cannot run without you then you do not own it, it owns you.

The part of this one that will sting is the exit math. When a buyer sees that the founder is load bearing, they do not walk away. They discount.

## In this episode

* Why a twenty year old could run a three million pound restaurant, and why the same kid could not be trusted with a company car

* How founders train the company to depend on them in the years before the first hire

* The first employee, and the loop where the owner ends up doing both jobs

* What a private equity buyer actually looks at, and why founder dependency turns into a price cut

* The split deal, roughly 40 percent up front and the rest tied to numbers you no longer control

* Why getting a company ready to sell starts about five years out

* Everybody overcomplicates it before they learn to simplify it

* The 25 year goal, and why anything shorter keeps the founder in the middle

* Do not be lazy with AI, and what lazy actually costs

## Timestamps

00:00 Intro

01:11 Fifteen years inside McDonald's, starting at sixteen

01:50 Taylorism, and a twenty year old running a three million pound restaurant

04:19 You do not own a business, your business owns you

04:54 How the dependency gets trained in from day one

07:32 The first hire, and why it often makes things worse

09:08 Influence instead of control

10:41 Choosing Scaling Up, and leaving after sixteen years

13:17 What a buyer looks at in due diligence

14:46 Why founder dependency becomes a discount

15:56 The 40 percent up front and the earnout behind it

17:40 Getting a business ready to sell, five years out

18:51 Complexity fails, simplicity scales

21:29 Steve Jobs, the first tenure and the second

23:45 Consistency as a strategy, McDonald's and Chick-fil-A

26:22 What he looks at on the first deep dive

28:00 What do you actually want out of your life

30:14 The 25 year goal

31:57 Why he wrote Your Business Sucks

36:42 Do not be lazy with AI

40:05 Where to find Peter

## Peter Boolkah

Known as The Transition Guy. Fifteen years at McDonald's, then twenty one years coaching owners across five continents, taking companies through to sale and IPO. His book is Your Business Sucks, on Amazon. He is at boolkah.com

## A note on the book

Peter mentions a 99 cent Kindle price near the end. That was a launch offer at the time we recorded, so check Amazon for the current price.

## One more thing

Most of what makes a business hard to sell is the stuff living in one person's head. That is the work I do at Front Range Systems: https://crm.frontrangesystems.com/discovery

Omar L. Harris ran a 900 person organization in Indonesia and nearly sank it with a handful of bad hires. To dig out, he wrote himself a manual. That manual became a book, the book became eight more, and the whole thing became a framework for the part of a business most founders treat as an afterthought.

Matt builds operating systems out of software. Omar builds them out of people. Same word, opposite raw material, and the conversation goes straight at where the two meet.

## In this episode

* Why a resume is a marketing document, and what actually predicts how someone shows up

* The difference between a personality test and a character test, which is what you choose under pressure

* Six hours with a team, fourteen teams, and a 30 point jump in engagement six weeks later

* Why culture built with a team sticks and culture handed to a team does not

* The three things that send any team back to square one

* The person who knows everything, and the incentive quietly paying them to stay that way

* Where AI stops being useful and human judgment takes over

## Timestamps

00:00 Intro

00:49 Nine books, and a novel that took twelve years

01:34 Rebuilding a 900 person organization in Indonesia

02:25 Grow With W.H.O.M., eleven years in the making

03:08 Why pedigree and references predict less than behavior

04:29 Character assessment versus personality assessment

05:17 Walking away from the corporate job, twice

06:27 What carries across every market he has worked in

08:26 What a culture operating system actually is

10:43 Forming, storming, norming, performing, and how to speed it up

11:43 The three things that send any team back to forming

14:30 Fourteen teams, six hours each, 30 points of engagement

16:19 What happens after the first engagement ends

17:20 Where AI stops and judgment starts

20:24 Who should not install a culture operating system

22:09 Tribal knowledge and the incentive behind it

24:29 The assessments he is certified on and how he uses them

26:10 Where to find Omar

## Omar L. Harris

Founder of Intent Consulting and author of nine books, including Leaderboard: The DNA of High Performing Teams and his latest, Grow With W.H.O.M. Former general manager for a pharmaceutical business in Indonesia, with earlier roles in Brazil and Turkey.

W.H.O.M. stands for Work Ethic, Heart, Optimism, Maturity. The book and the free character assessment are both at growwithwhom.com. He is on LinkedIn as Omar L. Harris.

## One more thing

If your business runs on what one person happens to remember, that is a systems problem before it is a people problem. That is the work I do at Front Range Systems: https://crm.frontrangesystems.com/discovery