📬 Imposter Syndrome: The First 90 Days

What if running a business felt like playing a strategy game, where every move is simulated in real-time?

Most finance teams are buried in static spreadsheets, forced to make decisions based on old data instead of real-time insights.

Runway founder Siqi Chen thinks that’s backwards. Finance shouldn’t just track history, it should shape the future.

In this exclusive interview, the Runway CEO…

• Explains how outdated finance tools keep companies stuck in reactive mode, making decisions too late to matter

• Argues that finance should feel more like a strategy game, where every move updates the future instantly

• Reveals what it takes to give every department, not just finance, the power to see the impact of their decisions before they even make them

Read the full interview.

Chris, the tech account executive from London asked:

As a CFO, what do you wish corporate salespeople understood that most don’t?

Chris - I’m glad you asked this question.

The number 1 thing tech sales execs need to understand about CFOs is… no, we don’t have 15 minutes to hop on a Zoom call to discuss our digital transformation priorities for 2025.

OK, I’m kidding… well kinda.

The key thing to understand is how damn busy we are.

We have less than a fraction of 1% of our time to allocate to responding to cold enterprise sales outreach. And we receive what feels like hundreds of emails per week.

And … IT ALL SOUNDS THE SAME.

So, first up, make sure the CFO is definitely the right contact for you.

For example, the CFO of a large company is not making decisions on who the company's printer paper supplier is. There is someone in the procurement team who is paid to solve this problem (among others). Find out who they are and contact them instead. Seriously, I get at least one inbound per week on this topic.

It’s easy to assume that because your pitch is saving the company money, it must be interesting to the CFO. Good salespeople understand that is not necessarily the case and do their homework.

Second, keep it short. Who are you, what are you selling, and why should we care? Make it easy for CFOs to digest your pitch.

Third, personalize it. Anything that feels generic or automated is going straight to the trash. Give us a sense that you have done your homework, you are targeting us for a reason.

You can show that by making sure your outreach is personal, specific, unique, relevant, and brief.

Finally, help us qualify our interest very quickly, and be honest if your solution doesn’t solve our problem. This is to help protect your time as much as ours.

Thanks for asking, Chris. The fact that you did suggests you are one of the good ones.

Mario from Croatia asked:

Would you use EBITDA as a starting point for valuations in cyclical sectors like construction, or would you rely on some other metric (or perhaps apply a different valuation methodology)? And how would you calculate the working capital peg in construction businesses, given that their working capital is influenced by project dynamics (projects extending above one year, phased payments, lots of advances received, etc.)? Many thanks!

Mario. Great question. Let’s-a go…

The technically sound answer, of course, is to build a cashflow forecast and discount it back to get a net present value. But if it were as simple as that, you wouldn’t be asking the question.

And it’s even harder in a cyclical industry like construction, where a change in interest rates or a GDP slow down could chop your demand forecast and project pipeline. So how would you build that long range forecast anyway?!

So, yes, I would revert to a multiple-based valuation method and double down on making sure you understand the current financial position of the business.

So that leaves two questions:

1. Multiple of what?

2. What multiple?

I’d start with EBITDA but adjust it to approximate a cash-based metric, deducting maintenance CapEx to get closer to an ‘EBITDA-CapEx’ proxy.

Then you need to make sure you normalize that for any one-offs. Project accounting can be lumpy, so you need to make sure you get to a ‘normalized’ level of EBITDA to reflect a true current 12-month activity pattern or the business. You could easily end up with a P&L with 14 months activity in it, by a quirk of GAAP.

The devil is in the details.

And how do you select a multiple? You are relying on transactional comps (either private deals or public stock prices discounted for illiquidity). Once you have some benchmarks, you can adjust that multiple for your ‘house view’ of where you are in the cycle. For example, if you think you are at the top of the cycle, you would discount that comparable multiple from a long-term risk-weighted industry average. Reflecting the downside risk.

None of this is exact science, of course. So lean into your understanding of your business and the assumptions that underpin other transactions and valuations in your industry.

Now, about your working capital peg. This is a crucial question in businesses that have long contract cycles. Especially those with project-based revenue accounting.

Ultimately, it’s about finding a fair level that reflects the normal levels of working capital you would expect in the business. there will be some assumptions from your normalized EBITDA calculations you can pull across here.

Some practical considerations:

• Look at average net working capital (ex-cash) as % of revenue over 3–5 years.

• Adjust for abnormal spikes due to the timing of large projects or advance payments.

• Consider the stage of projects in WIP (early-stage projects often distort the balance sheet).

• Treat "advances received" as potentially non-recurring or project-tied liabilities that shouldn't be part of normalized working capital.

• And critically, make sure your assumptions on working capital align with your normalization of EBITDA assumptions.

There is a lot to work through here, though, so make sure you are well-advised!

Thanks for your question.

Datman from Australia asked:

I'm starting a new job in the next few weeks as a supply chain Finance Business Patner. Whenever I start a new role, I go through a severe case of "Imposter" syndrome.

Do you have any home remedies on how to navigate the first 90 days and limit this "Imposter" feeling as much as possible?

Thanks for the question, Datman. Or should I call you Bruce Dwayne.

Congratulations on the new role.

First up, imposter syndrome is normal when starting a new job. You aren’t on your own. I have had it at every job. And still get it every time I hit send on an email that goes to 50,000 CFOs all over the world twice per week.

It’s a sign you are pushing yourself into a zone where you grow, and that’s important. So it’s a good thing. Don’t hide from it. Embrace it.

Secondly, you got the job because your new boss decided you were better than all the other people who interviewed. That should give you confidence.

Next, you are going to go through the Happy-Sad-Dumb-Smart matrix. I wrote about that here. It’ll feel painful for a bit, but you’ll be fine. And knowing you’ll be fine is what will get you through it.

Onto more practical coping strategies. Two spring to mind:

1. Work your ass off. It’ll help you get through it sooner and stronger.

2. Seek small wins. Try and bank small successes in your first few months. It’ll help build your confidence and show your new team some early value.

Best of luck with the new role, Datman.

Every week I’ll share a book I loved or found useful.

A few of the biggest stories that every CFO is paying close attention to. This is the section you probably don’t want to see your name in.

Ex-Tesla CFO Leads Employee-Rewards Startup’s Funding Round in First Major Venture Since Exit

Former Tesla CFO Zach Kirkhorn has put his head up for the first time since he left the role last year. If there is one person I’d bet on, it’d be the guy who was able to last as Elon’s CFO for 4 years (and leave on his own terms).

Deutsche Bank picks Morgan Stanley vet for CFO

File this one under ‘difficult.’ Deutsche Bank appears to finally be on the other side of countless scandals/f*ck ups over the past decade, but now the German economy is an absolute sh*tshow. Raja Akram has a big job on his hands.

ICYMI, some of my favorite finance/business social media posts from this week. In the words of Kendall Roy, “all bangers, all the time”:

ChatGPT’s new image generation tool is very cool. Future merch plan?

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Let me know what you thought of today’s Mailbag. Just hit reply… I read every message.

In case you missed it on Saturday, we dove into delivering CapEx projects on time, on budget, and on spec. You can catch up here.

Disclaimer: I am not your accountant, tax advisor, lawyer, CFO, director, or friend. Well, maybe I’m your friend, but I am not any of those other things. Everything I publish represents my opinions only, not advice. Running the finances for a company is serious business, and you should take the proper advice you need.