Imposter Syndrome

2014-12-15 by Jason Freedman



In May 2009, I walked into Y Combinator. My company, FlightCaster, had just gotten accepted and this was our intro session to the group. And kind of like the Dean of Admissions on the first day of freshman orientation, Jessica got up and recounted a bunch of stats about how cool our summer 2009 batch of Y Combinator was.

this company is taking on Google Analytics…(MixPanel)

and this company already has 1 million downloads…(Bump)

and this company will change banking forever…(WePay)

and on and on…


Becoming more formidable

2014-12-05 by Jason Freedman


“The founder who handles fundraising should be the CEO, who should in turn be the most formidable of the founders.”

-Paul Graham in his epic Fundraising How To guide

 inspiring fear or respect through being impressively large, powerful, intense, or capable.



As a startup founder, the idea of pitching was always compelling.  I just knew that if I could get in front of the right people, I could personally persuade them.  So when I was getting ready to pitch FlightCaster during the 2009 YCombinator demo day, I knew it was my time to shine.

When I got up to the stage, I was able to tell a story and wow the audience. In fact, one of the other founders told me afterwards that he felt like I could sell anything,

It was a good moment.

Continue… Reborn. Actually, better.

2014-12-03 by Jason Freedman



I bet a lot of you remember that app called It was a little startup that hooked into your various calendars and would allow people who wanted to make an appointment with you to self-schedule times in your open slots. It got all the little user experience pieces right such that I found that lots of people were simply sending their private link every time they wanted to schedule an appointment.

But this was like five years ago, and then Blackberry bought them. And then as so often happened, they stagnated. Finally, several years ago Blackberry discontinued and all of us went back to the myriad of crappy ways that we manage scheduling.

There are a lot of methods and apps out there that people use. I wanted to take a few minutes and alert you to Calendly. It’s basically reborn. They could very well object to that statement because the reality is the UI and overall experience is much better. But for those of you who were fans, you will recognize it immediately. Continue…

Sort of Obstreperous

2014-11-25 by Jason Freedman


I fucked up with one my co-workers here at 42Floors.

I had to apologize and take it all back.  At least I was fortunate enough to have the opportunity.  My big transgression?

I tried to tell him what to do. Continue…

Surviving the Series A Crunch

2014-11-19 by Jason Freedman

'So, it's taken you six months to finally finish the report on our financial crisis and your solution is: 'We need to make more money'.'


I just had a crappy conversation with a good friend of mine. It’s the third crappy conversation I’ve had in the past week, so it’s probably time to write a post about this.

My friend did Y Combinator with me, raising a-million-and-a-half with a good valuation from good investors. He’s now coming towards the end of that runway. He called me to talk about fundraising. We actually use his product and like it. So I’m not only a fan of his personally, but I like what he’s doing.

I asked his to give me the rundown on the metrics.

$50,000 a month in revenue, growing 9% month-over-month

Headcount of 8, mostly engineers

All in, $90,000 a month in costs, $40,000 a month burn

$160,000 in the bank, 4 months of runway left

From his perspective, things were finally on track. After some strategy shifts in product and working through some cofounder issues, things were finally feeling really solid in the company. Anecdotally, he knew that customers were really happy with him and his revenue number kept growing. Fifty thousand dollars a month is proof that real people were paying for his product. And with $160,000 in the bank, he felt like he still had plenty of runway left. Fundraising took a month or two during the seed round and he’s got four months left, so thus the reach out to begin the process.

For a few minutes, I walked the fine line of congratulating him on all the progress before diving into the meat of the issue. And that is this:


You’re only doing medium well. And medium well might not get you anywhere.


The Math of Split Testing Part 3: The Chance of being Similar

2014-06-24 by Aaron O'Connell

Sometimes we want to verify that a new design will convert at nearly the same rate as an old design. Split tests of this type are not intended to find conversion rate wins, but rather to ensure that the new design is not “too much worse” than the old design. Here, we demonstrate how to analyze a split test of this sort and present an approximate formula to quickly calculate the chance that there is an acceptable difference between the conversion rates of the new and old designs.

Let’s say that we think that the design of our website is starting to look a little outdated and needs to be redone. In this scenario, we’re not really looking to increase conversion rate. We’d be happy to keep our current conversion rate and just make the website look a little more hip. To verify that our new design (branch B) converts at a similar rate Continue…

In Defense of Recruiters

2014-06-17 by Jason Freedman

Recruiter on line three cartoon

Ever since we wrote that post where we trolled annoying recruiters, I’ve had quite a few conversations with entrepreneur friends about this subject.  Overwhelmingly, most of these founders said something along the lines of, “recruiters are just worthless.” Obviously, I could see why they would think so; I used to feel the same way.

I didn’t use a recruiter to hire anyone for either of my first two companies or for the first ten people at 42Floors.  The entirety of my interaction with recruiters was trying to get them to stop spamming us about their “MIT Alumni at Google who is a Ruby Ninja Rockstar.” Or even worse, that same recruiter spamming every engineer in our company promising to help them find a better job.

However, we’ve actually used recruiters very successfully at 42Floors, and all my friends who are claiming that all recruiters are worthless tend to be seed stage or first-time entrepreneurs that have not yet gotten to the best use cases for recruiters.

So I thought it might be helpful to show the different ways we have successfully used recruiters to scale 42Floors.   Continue…

The Math of Split Testing Part 2: Chance of Being Better

2014-06-10 by Aaron O'Connell

Split tests are a powerful way to determine if a new design has outperformed an old design. Here, we present the math necessary to empirically state the chance that a new design (branch B) is better than an old design (branch A). We walk through the problem with numerical simulations and present an approximate formula to easily determine the winner of an A/B test.

Split testing is the preferred way to collect data for fact based decision making. Longitudinal studies are subject to underlying market trends and are not well suited for conversion rate experiments. If, for example, you roll out a new version of your website in April and notice a decrease in conversion rate, you may be tempted to say that your new website design is a failure. But maybe April was just a bad month. If instead you had set up a split test for your new design, you could eliminate this concern. While overall conversions may have fallen in April, it could easily be the case that the results of a split test measurement would have shown the new website design performed 20% better than original design, with 95% chance that the new design is better than the original.

In this post, we’ll introduce the math necessary to declare branch A or branch B the winner of the split test. Continue…

Node FTW

2014-06-09 by Aaron O'Connell

Want to crunch some numbers? Node is 10x faster than Ruby.

I used to do a lot of scientific computing. My work environment had both Matlab and NumPy/SciPy all tricked out. These days I don’t do too much number crunching, spending most of my time with Ruby and JavaScript. Continue…

The Math of Split Testing Part 1: Statistical Sampling Uncertainty

2014-06-05 by Aaron O'Connell

Here we introduce the idea of statistical sampling uncertainty in the content of conversion rate optimization for website design. We begin by illustrating how successive trials of coin flips result in the binomial mass function. Then, we turn the problem on its head and show how to describe the conversion rate of a funnel event (the true bias of a weighted coin) by examining the results of a series of conversions. Finally, we discuss the validity of the Wald and Wilson confidence interval approximations to further quantify the conversion rate confidence interval.

This series of blog posts focuses on the math needed to make fact based decisions as quickly as possible. Many websites have clear actions they wish their visitors would take. A commerce website, for example, would like it if their visitors would purchase a product. While it may be reasonable to focus solely on the number of unique visitors that purchase a product (total conversions), in many cases it is useful to to think about the customer experience as a series of actions that lead down a funnel. Continue…