We live in an extraordinary moment where startups that IPO’d after 2000 dominate the major stock indices, yet among the 100 largest charities on this list, more organizations predate the 20th Century than follow the founding of Google.
To put this in plain terms: Six of the top 100 charities on the list compiled by Forbes were founded after the year 2000. 15 were founded prior to the year 1900. The median non-profit was founded in 1950. You can see the full distribution here.
The US remains an incredibly generous country, and while giving has decreased by…
As we approach the end of COVID, many who experimented with life in the Hudson Valley or Tahoe, or those new urbanists who flocked to cities like Miami or Austin, or back home to the midwest, will have some decisions to make.
Primarily, should I stay or should I go?
Over my professional career, I’ve moved from LA > Boston > NYC > SF > NYC and brought a family along on several of those journeys. Recently some friends have asked for my POV/tips on relocation, and I thought they might be useful to a wider audience.
⛵️ Burn the boats
…
Today Olo becomes $OLO. I’ve had the honor and privilege of being alongside Noah Glass from the get-go. Today’s IPO is a major milestone, and I want to share a couple of small reflections:
⏳ You can’t be too early
👣 You have to prepare for a long journey
⏳ You can’t be too early
There’s a saying in VC that being too early as a startup is as bad as being wrong. I think this is incorrect. Noah started Olo in 2005 — two years before the iPhone kicked off the smartphone revolution. These were the early websites:
Recently, S’well bottle founder and friend Sarah Kauss met with our portfolio and shared brilliant advice. There were three bits in particular that we wanted to share with a wider audience:
🚪 Search for “side doors”
👩⚖️Your brand > Your legal budget
🌷Push Up to Push Out
Background: This interview is a good overview of Sarah’s journey from accountant to entrepreneur and how she redefined a commodified category and built a $100M+ business in the process. Please give it a listen!
🚪 Search for “side doors”
Sarah wanted S’well to be an aspirational, fashion-forward brand. Celebrity endorsements are a proven way to…
Encouraging founders to raise less VC feels like telling people to eat spinach when everyone in the startup world is munching on Shake Shack, but it has benefits:
🥇 Better partners
💰 Smaller preference stack
🛣️ More Options
😬 Less stress
💸 Self-control
⏱️ Time to grow
VCs telling founders to consider smaller funding rounds is counterintuitive.
“Don’t VCs want the highest markup?”
“Don’t VCs want their portfolio companies to have more money in the bank?”
“Doesn’t it validate his/her investment?”
It’s more complicated …
🥇 Better partners
Optimizing for price makes sense in the moment, but don’t prioritize short-term…
An architect talks to three masons working side-by-side and asks about their work.
🧱 “I’m laying brick…” says the first.
🏗️ “I’m putting up a wall,” answers the second.
⛪️ “I’m building a cathedral!” Exclaims the third. This parable of POV can be applied to startups:
This allegory is typically deployed when trying to make an unpleasant task sound more palatable. The cathedral response is supposed to be the “right” answer, but the story’s moral is really a reminder that you need to be able to think/talk at multiple levels of abstraction.
Whether you are pitching VCs…
Over the last five years, Google/Apple/Facebook/Amazon (GAFA) have gone from being inspirations to … competitive sharks that can easily gobble up the market share and margin of the smaller startups surrounding them.
Here’s some advice for founders in the era of Big Tech…
🐸 Don’t get complacent
The primary danger that Google, Facebook, et al. pose to startups is in getting entrepreneurs hooked on *seemingly* cheap growth. The targeted advertising these platforms provide produces a quick revenue boost that can scale surprisingly well.
Unfortunately, the good times don’t necessarily last. Startups see diminishing returns, competition arrives, CAC can rise to unsustainable…
Clubhouse, and conferences generally, are a great leveling tool where an entry-level engineer can ask unfiltered questions of a captain of industry.
This is an opportunity that should not be wasted — or hoarded!
Here are a few simple tips that will raise your question asking game:
❓ Start questions with an “H” or “W,” not “I”
🚫 No two-part questions
📏 Know your limits
📌 Formulate crisp queries
🕳️ Avoid “talking point” traps
🙃 Be Provocative
Let me expand:
❓ Start questions with an “H” or “W,” not “I”
Ask questions that other people will benefit from.
Questions that start with who, what, when, where, why…
By Brent Willess, Associate
One surprising thing I’ve learned in my first year in VC is how “We’re not raising right now” is a powerful phrase an entrepreneur can say to an investor. A big reason is that it tends to uncover other aspects of the business, for example:
“We got creative with marketing”
Startups that can self-fund also tend to be more creative about their go-to-market strategies. Expensive paid advertising is seen as a last resort and clever, low-cost alternatives are sought out and uncovered.
“We have strong margins”
The freedom to forego fundraising usually comes from profitability derived from predictable revenue and stronger than average margins. …
By David Frankel, Managing Partner
Offering internal recruiting bonuses is a fast way to scale talent at a startup. This is expedient and powerful. But as for any sales comp, incentives are key.
Should bonuses be paid in full at the hire?
Or split, with a balance paid at a retention cliff?
My preference is that the bonus should be split, with 50% at hire, and 50% reserved for a milestone, typically the one-year anniversary. Some argue that retention is the job of direct managers and the executive team, and that’s a very fair point.
Still, if you’ll forgive a…
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