By David Frankel

Founder 1: Runs startup for five years. Sells for ~$100M. Makes $30M.

Founder 2: Running startup for ten years (and counting). Valued at ~$1B. Founder shares valued at $30M.

Which founder would you rather be?

There is no easy — or correct — answer to this question. These founders have different life situations and ambitions. However, I don’t think VCs do enough to highlight the financial risks founders take by getting on the fundraising treadmill.

Raising venture capital increases the theoretical value of a startup and the paper wealth of its founders. It also reduces the number…


By Joseph Flaherty

I think tech cynicism has taken hold in part because we can’t fully measure many of its benefits. CAC, LTV, and ARR are well understood, so I want to propose a few new metrics that capture the bounties of the internet — Consider:

👶 DIAPER

💄 GLAM

🎨 ART

🧂 SALT BAE

💍 I DO

👶 Daily Images Add to Parental Enjoyment & Rejoicing (DIAPER)

What is the improvement in human happiness caused by ready access to cell phone cameras and the ability to capture more spontaneous moments of your child’s life?

Imagine a working parent pre-camera phone. What would they pay for a video that captures…


By Micah Rosenbloom

Fundraising is happening at a torrid pace.

Speed dating and shotgun weddings between founders and VCs are happening everywhere and will lead to many unhappy unions.

Since there are no prenups at startups, here are questions you *must* ask before you sign that term sheet!

🔭 Will you lead?

Lead investors are the most difficult to find and must be prioritized. Don’t waste time having extensive conversations with any investor until you know the answer to this question.

🐘 How big is this check relative to your fund?

You want to be sure the VCs are making an investment, not buying an option to invest more later if you enjoy success.


By David Frankel

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…


By Micah Rosenbloom

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


By David Frankel

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:


By Micah Rosenbloom

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…


By Micah Rosenbloom

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…


By Joseph Flaherty

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…


By David Frankel

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…

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