Defending a Startups Greatest Asset through Recession & Recovery

Yesterday, Office Hours welcomed Lee Kirkpatrick, former CFO at Twilio to share his experiences managing through three different recessions: the dotcom era, the Global Financial Crisis, and today.

Lee headed finance for the company from $15m in ARR to more than $1b. In addition, Lee shared his view on usage-based pricing and defending a startup’s great asset, talent, from poaching during the next recovery.

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How VCs Value Rainbow Foals in 2022

When Aileen Lee published “Welcome to the Unicorn Club” - the article that coined the word unicorn for a $1b startup - the average public SaaS company commanded a market cap of $1.5b.

I remember thinking a $1b M&A or IPO was so rare an investor might hope to achieve it once or twice in a career. Fewer than 15 SaaS companies traded on public exchanges then. With at least 20 firms and several partners per firm chasing unicorns, upstarts faced stiff odds.

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Bezos' Shareholder Letter in 2000

OUCH. It’s been a brutal year for many in the capital markets and certainly for Amazon.com shareholders. As of this writing, our shares are down more than 80 percent from when I wrote you last year.

Jeff Bezos wrote this to start his annual shareholder letter in the year 2000. But he might have written it today. Amazon stock reached an all time high of $5.33 before falling to $0.298.

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The Most Popular Financing Round in 2022

The round extension is the most popular fundraising round today. You won’t find statistics detailing their rise in PitchBook or Crunchbase, but “reopening the last round” or “raising a round extension” precede pitches Startupland today.

How does an extension impact a company’s cap table on average?

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Round dilution from VC dollars has been declining for the past decade. These figures exclude employee stock option (ESOP) dilution.

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What's Better than a Cookie? A Wallet - How Crypto Will Revolutionize Marketing

Suppose a VC gave you, a web3 marketer, $50m to spend to acquire as many users as possible? How would you do it? Conference sponsorships? Cross-DAO messaging in Discord? Sponsored social? It would be a challenge to drive any efficiency.

The past isn’t much help, either. Web2 marketing channels don’t apply because they employ third-party cookies, a technology Google will phase out at the end of 2022. Third-party cookies enable marketers to advertise to users who they haven’t “met” online yet. Third-party cookies encrust information about which sites I’ve visited.

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Office Hours with Lee Kirkpatrick, former Twilio CFO on Managing through Turbulence

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Lee Kirkpatrick is no stranger to downturns. During the dotcom crash in 2001, the Global Financial Crisis of 2008, and the SaaS corrections in 2014, 2016, and 2018, Lee was either COO/CFO or CFO at Twilio, SAY Media, and Ofoto.

In addition to his experience navigating financial markets, Lee oversaw the finance function at one of the most successful usage-based billing companies. Usage-based billing - the practice of charging customers by consumption rather than subscription - has become top of mind for many startups seeking to align their success with customer needs.

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The New Key Competitive Advantage for Web3 Startups

The web3 market’s collapse in the last few weeks will reverberate across the ecosystem, especially for marketing teams.

Blind airdrops, multi-million dollar ecosystem funds, sports team sponsorships - predominant marketing techniques redolent of the bull market - won’t last.

A tighter fundraising market and competition will catalyze web3 marketers to adopt a new discipline. Why? Marketing efficiency is a vital competitive advantage.

While this is just as true in web2 as in web3, crypto brings new complexities that create opportunity. Token efficiency accounting isn’t widespread. For example, most web3 companies don’t consider tokens as a cost-of-customer acquisition, but they ought to be. We need to invent new marketing math.

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Is a 10% Reduction in Staff a Layoff?

Should a 10% reduction in staff be considered a layoff? In one sense, yes, because on a particular day, a collection of employees no longer work at a startup. But a 10% layoff shouldn’t confer messages of a financially strapped business.

Consider the average annual employee attrition in a startup ranges between 13% and 25%. A 10% reduction-in-force (RIF) is less than the quantum of employees the business would have expected to lose throughout the year.

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The Macroeconomic Signal to Watch for Software & Infrastructure Startups

As we navigate this bear market, I’m keeping my eye on broader market data points. A broad software buyer index would be the best metric to understand how buyer preferences are changing across the market. Fortunately, it exists.

Large SaaS and IaaS vendors are precisely that: indexes of software buyers. Amazon Web Services and Azure, the business units inside Amazon and Microsoft serve and sell to small, medium, and large companies in every major geography. So do Salesforce. ServiceNow. Adobe. Palo Alto Networks.

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