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Starting Line's Operating Manual (How We Think)
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Starting Line Operating Manual

Welcome! Weren't expecting this? That's OK! FYI that Starting Line's home website is still open in your prior window.

This repository exists because we recognize that entrepreneurs struggle to both properly understand and connect with prospective investors. Our dream is that this operating manual provides all the information you could possibly want to know about us; and we will continually update it to fill in holes that are discovered.

This manual was inspired by our friends at Bloomberg Beta (one of our first investors) who are also committed to radical transparency.

Table of Contents

What We Invest In

Starting Line is a thematic early stage venture capital fund focused on investing in consumer services and products that are both cheaper and better.

We, like many Americans, were struck by the November 2016 elections and it was one of the inspirations behind the founding of this platform. Technology has the potential to democratize access to information, wealth and opportunity; however, over the past decade, the gap between the 1% and the 99% has widened substantially. We invest where we see opportunities to make products and services available to a broad range of Americans - not build incremental services for the affluent.

We do not invest in enterprise software nor affluence or luxury focused products (unless they are substantially more affordable than their peers).

The Checks We Write

We are a first check venture capital fund, meaning that we aim to anchor true seed rounds with check sizes ranging from $750,000 - $1,250,000 in rounds ranging from $1 - $5M. Our sweet spot within that range is leading $1M into a $2.5M seed round.

Our fund is unique in that we reserve very little money for follow-ons into future rounds. We are blessed with a risk tolerant group of LPs who have approved a fund structure whereby we invest 80% of our capital up front into first checks and reserve only 20% for follow-ons. We guarantee each investment we seed a follow-on check of $100,000 irrespective of progress or next round size.

We believe this unorthodox structure is beneficial for early stage founders for a variety of reasons:

  1. It allows founders & investors to be deeply aligned across a spectrum of goals and outcomes. We are both fighting for the same oxygen in future rounds.
  2. It generates a strong market signal given that Starting Line only makes ~5-6 new investments per year. (We do not buy "options.")
  3. It removes any negative market signaling from future financings.
  4. It allows founders to more quickly close their seed rounds and get back to build their business - rather than spending months accumulating a series of smaller checks.

Geographic Focus

Starting Line is HQ'd in Chicago, IL and we are highly biased towards our hometown of Chicago and other underserved communities. However, we have no formal geographic policy - and instead are inspired by founders aiming to solve problems for average, everyday Americans. Our fund investments have ranged from New York to Austin and our angel investments have criss-crossed the country from SF to NYC to Seattle and everything in between.

Getting in Touch

There is no right or wrong way to get in touch with us. A great cold e-mail is far superior than an intro from someone we don't know all that well.

We recognize that as an entrepreneur it can often be difficult to gauge whom we know "well," so in general its best to bias towards introductions through founders we've invested in, or even employees at the companies we've invested in. As early stage investors, we often have 1:1 relationships with many of the first 50+ employees.

How We Think

We try to produce a substantial amount of content and make it accessible widely. We even took the drastic step of open-sourcing our quarterly LP letters so you can gain insight into the trends we're following, how we see the world, and the narrative we're telling our own investors. Here is a non-exhaustive list of ways to learn more about us:

Our Quarterly LP Letters



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