Lessons from a fallen CEO - FP Advance

Lessons from a fallen CEO

BY brett

Man falling from a ladder for lessons learned fallen CEO

Uber, the American multinational ride-sharing company, grew from 400 team members to 14,000, in only 7 years. 

Just before he was fired by the Uber board, Travis Kalanick was facing major personal issues: “His mother had died in a boating accident that also left his father seriously injured.1

He also faced a well-documented list of issues within Uber that were under serious public scrutiny. 

Apparently, while at his Dad’s hospital bedside, he penned a letter to Uber employees which was never sent. It’s 2000 words, and I’ve included a link to it in full at the end of this article if you’re interested. 

I’m going to focus on the first five paragraphs only because even in that short span there are five great lessons for the owners of Financial Planning businesses.

Travis Kalanick letter (never sent) to the team at Uber: 


Over the last seven years, our company has grown a lot — but it hasn’t grown up. 

I’ve been an entrepreneur my whole life. Most of the time, I’ve been on the brink of imminent failure and bankruptcy. I was never focused on building thriving organizations. I was mostly just struggling to survive.

When Uber took off, for the first time in my life I was leading an organization that wasn’t on the brink of failure each day. In just the last three and a half years, our service and our company has grown at an unprecedented rate…

…As we grew, I held on to too many things that helped me survive and build a great company, but at scale became ever-increasing liabilities.

I put growing our business ahead of properly scaling our internal culture and organization.”

Let’s look at the lessons in each one.

1. Have You Grown Up?

If you’re growing and successful, each year takes you into new territory that you’ve never been in before. New challenges with people, process, technology etc; none of which you’ve got a ready made playbook to deal with. You’re sort of making it up as you go along.

Sure, there are people out there you can go to for help, but even choosing the ‘right’ one of those is something you’ve never done before. Just add it to your list. 

The stress of all this ‘newness’ can be invigorating, but sometimes it can become heavy, or even overwhelming. What to do?

There’s only one real choice in my view; grow.


Work on you.

As I’ve written before, your business’s growth won’t outstrip your own personal growth. 

When you’re running a growing business working on you doesn’t mean getting more technical qualifications, or more selling skills. It means learning to think like a business person. 

Look for courses, mastermind groups and mentors that can help develop that part of yourself. 

Growing up means focusing on the inputs that will lay a strong foundation in your business, upon which you can build, grow, and scale. 

The core inputs to work on are:

2. Do You Feel The Financial Strain?

As Kalanick alluded to, a lot of the time when you’re running a business you can feel “on the brink of imminent failure and bankruptcy. I was never focused on building thriving organizations. I was mostly just struggling to survive.”

Some business owners reading this might be feeling the same way. 

If you run a mature financial planning business people might be telling you it’s worth millions. It might even be true. 

But you can’t spend it, or eat it right now can you? It’s only on paper. 

So you can still feel poor, even while others might see you as rich. 

How do you explain that feeling to someone who hasn’t walked your path? Your friends, family and neighbours who are employees for example. They just don’t get it, and if you try to explain it, you might come across sounding like a spoiled brat. 

I know how you feel. All business owners do.

However, don’t let the fears that arise as a result of this situation run the show. 

How do you do this?

Focus on the inputs every day, not the results or outcomes:

  • Keep a close eye on your expenses and cash flow.
  • Know when to spend money on developing your business, and when to keep your powder dry for any tough times ahead.
  • Focus on your meeting rhythm: annual business planning, quarterly goals and  learning reviews, and weekly leadership team meetings.
  • Develop people so they can become the future leaders in your business.
  • Don’t look for new technology: focus on solving the challenges your clients face, and be open to technological solutions that allow you to do that better, faster, and more simply.
  • Build a robust and healthy culture, by talking constantly about your core values.
  • Stay personally focused on doing a great job every day; as a leader, decision maker, and financial planner in your business.

3. Have You Shifted Gears?

Light bulb made of words like Visio, Future, Plan

Are you running a business that’s started to see the growth you’ve always wanted?

That type of growth requires a shift in gears: 

  • Who else do you need to bring in to strengthen the leadership team?
  • What new processes are required? 
  • What new technologies? 
  • What new people?
  • What inputs and foundations need to be built to ensure the long-term survival and prosperity of the company?

Are you focused on those things?

In the business planning process we teach at FP Advance, one of our steps asks owners to set a Big Hairy Audacious Goal (BHAG) for 10 years out. Our recommendation is that this goal should feel about 20% believable. To be honest, 20% believable feels almost unbelievable. If it’s not that scary, it’s not a BHAG.

But that’s not the important part of this step in the business planning process. 

We also ask owners to think about the five key steps they will need to take to bring their 10 year vision to fruition. This is the key.

For example, you might have a 10 year BHAG to be the best known, go-to financial planning firm in your area or region. What will have to happen to bring that about from where you are? 

Here are some example steps I thought of:

a.) Create a world class team of advisers and technical staff that create the core culture and standards for what amazing Financial Planning looks like.

b.) Become world class at marketing and promotion to attract a sustainable flow of ideal clients.

c.) Create depth of leadership throughout the organisation – mentor and bring through talent that is capable of running the business in the future.

d.) Partner with complimentary or adjacent service providers who add value to our clients and are also world class in their space – leverage skills and clients wherever possible.

e.) Be masters of execution daily, weekly, monthly, quarterly, annually. In the words of Epicticus, “I am at the Olympics, The competition is now, today.”

Once you have identified your five key steps, it takes you to a different place. By working on these issues now, you are laying strong foundations for the future.

4. Are You Holding On To Too Many Things?

I see business owners doing this all the time. They can’t delegate. 


Sometimes it’s because they’ve hired the wrong people. If you can’t trust someone to do it to the standard, then that’s a valid reason to not delegate.  

However, before you jump to that defense, ask yourself this question:

How good were you 10 years ago?

Not as good as you are today is the answer you’re looking for. 

How did you learn what you know now? 

Through making an endless series of mistakes; mostly small, sometimes big. 

That’s how your team learn too. Please let them fail, and then support them and help them unpick the learning opportunity within each failure. Trust good people to figure it out with your help and mentorship.

Stop being the indispensable expert in your own firm and start being a coach to your team.

5. How’s Your Culture Coming Along?

A good culture can sort out a lot of your potential growing pains. It’s vital to share values, by telling stories and catching each other acting in accordance with, or against, the business’s core values. 

For example, if you have a growth target, but one of your core values is to “Always do the right thing by the client”, you’ll rarely suffer from advisers or the team doing things that let you hit a short-term target, whilst doing something that undermines the long-term reputation and success of the company.

To Conclude:

As someone said to me years ago, “Financial Planning is a great get rich slow business.” 

We’ll probably never have to deal with the level of expansion faced by Uber and other fast growth companies. Yet there are some valuable business lessons from observing how these firms get it right and get it wrong. 

How well are you managing your firm’s growth?

Let me know how you go.

PS: I first saw this via Verne Harnish’s weekly email “Verne’s Insights”. The full letter from Travis Kalanick can be seen here, on Gizmodo.

1 (Source: Gizmodo – Exclusive: The Letter Travis Kalanick Never Sent)

Stop being the indispensable expert in your own firm and start being a coach to your team.

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ABOUT BRETT DAVIDSON When you work with FP Advance you work with me, Brett Davidson, directly. My motto is ‘advise better, live better’ and I practice what I preach. I’m straight talking and get to the heart of an issue quickly. There’s no beating about the bush, just a focus on helping things improve. Ask my clients – what I teach works.