25 Epic, Must-Read Blog Posts About Fundraising

02/08/2016 | By Alex Iskold

This post originally appeared on blog.up.co

In my capacity as the Managing Director at the Techstars NYC Accelerator, I spend a lot of time with founders on getting funding. Raising money is a complex and rigorous process. It requires preparation and precision.

I’ve been writing extensively on the topic here on my blog. I’ve been also collecting the best articles I find around the web. In this post, I’ve compiled the best writing I found on the topic with brief commentary about each post.

1. Metrics Every Entrepreneur Should Know by Heart

by Elizabeth Kraus of MergeLane

Having solid metrics is a huge benefit for a seed round and an absolute must for series A and beyond. If the founder can’t articulate metrics & numbers around the business, investors are very likely to pass. Read this post to know what metrics matter.

2. Sixteen Startup Metrics

by Jeff Jordan of A16Z

Team at A16Z pulled together an awesome post on metrics that matter. If CAC, LTV, GMV aren’t in your vocabulary yet, jump in.

3. Startup Growth Calculator

by Trevor Blackwell of Y Combinator

Trying to figure out how much capital to raise? When you will raise profitability? Use this awesome tool from Trevor. Super helpful. Also check out my post on How Much Capital to Raise.

4. Nine seed funding gotchas 

by Alex Iskold of Techstars

First time, and even serial founders make mistakes during fundraising. Most typical? Not being prepared. Other mistakes are doing it too early, or without traction. Read this post to learn what may go wrong in the typical fundraising.

5. Eight Things That Make Investors Cringe

by Lili Balfour of Atelier Advisors

In this fun, and spot on post Lili outlines things that drive investors crazy. Some include lies, stupidity, cluelessness. Read on.

6. Invest in Lines, not Dots

by Mark Suster of Upfront Ventures

Founders and Venture Capitalists have a different view of the fundraising process. Founders want checks fast, while VCs balance strong inclination towards a no with FOMO. In this classic post, Mark explains that the key to fundraising is building a relationship. Check out the related post I wrote about avoiding Happy Ears.

7. Like a First Date

by Joanne Wilson

Fundraising is a little bit like dating. Go too fast or too slow and it won’t work. What to do and what not to do is illuminated by Joanne Wilson, a prolific angel investor in NYC in this Wall Street Journal post.

8. Eight Things You Need To Know about Raising Venture Capital

by Alex Iskold of Techstars

Raising VC is difficult. A lot needs to come together. But what are some of the less obvious things? In this post we talk about things ranging from venture-backable businesses to partner dynamics and fund cycles.

9. Micro VC

by Shaun Abrahamson Greatest Good

Micro VCs are a new type of venture capitalists. They typically right smaller checks compare to VCs but bigger than angels do. Micro VCs play critical role in both seed and series A stage companies. Shaun’s epic post demystifies and breaks down all you need to know about Micro VC.

10. Raising a Seed Round

by Steve Schlafman of RRE Ventures

An epic deck that walks you through what you need to put together to raise a seed round. A ton of awesome information, with bonus material for NYC founders. For additional info on the topic read my post on putting together a Perfect Deck for Seed Round.

11. Everything you ever wanted to know about convertible note seed financings

by Scott Walker of Walker Corporate Law

Ah the convertible debt. Hated and loved by everyone. It's quick to do but what are the consequences? Scott talks about the good, the bad and the very ugly of convertible debt. For more on the topic read these excellent posts by Mark Suster and Brad Feld.

12. Six Body Language Mistakes You Don’t Know You Are Making

by Shane Jones of The Press Box

Fundraising is as much art as science. When founders meet investors they show them decks and talk about the business. But the deck is not the only thing investors look at. They read founders body language and pay close attention to their emotions. This fascinating post eliminates what not to do during the pitch meetings.

13. Everything you wanted to know about VC Liquidation Preferences

by Bo Yaghmaie of Cooley 

Liq prefs. They are no good, right? Well some are and some are okay. Read this excellent post by Bo to learn all about Liquidation preferences and how they impact your outcome as a founder.

14. Valuation and Option Pool

by Fred Wilson of Union Square Ventures

Option pool is a tool for you to attract talent and give them skin in the game, right? Sure. It is that a lot more. Investors ask that option pool is plenty and comes out of so-called pre-money valuation. What does that mean and why? Read this excellent post by Fred to find out.

15. Want to know how VCs calculate valuation differently from the Founders?

by Mark Suster of Upfront Ventures

Founders fixate on pre-money valuation. Investors are all about % of ownership. There are tricks to every single negotiation and VCs know the tricks. Mark Suster opens up and tells you like it is.

16. Venture Capital Deal Algebra

by Brad Feld of Foundry Group

The exact calculations of any funding round are kind of like voodoo science. Well not kind of, it is that. Complex spreadsheets, army of lawyers, and a ton of back and forth. Brad sheds light on how the calculations actually work.  While at it, go read another excellent post by Brad on what he thinks about seed investing.

17. Dial-For-Dollar Calls From Some VC Associates

by Bilal Zuberi of Lux Capital

Got a call from an Associate – take it or pass? Who are these Associates and what is their agenda? Read this great rant on the topic from a former associate and now partner.

18. Why Maximizing Your Valuation Maybe Minimizing Your Chance for Success

by Micah Baldwin of Amazon

Founders are obsessed with valuation, while VCs are focused on ownership. Micah explains in this fantastic post why it makes sense to raise on the lower valuation in the earlier days of the company vs. raising high early and then struggling to grow into the valuation. For another excellent take on this, read Fred Wilson’s The Valuation Trap.

19. Beware of Post Money Trap

by Albert Wenger of Union Square Ventures

How investors think about post-money and why it is important to keep it as low as you can. Sage advice from Albert. Fred Wilson also comments.

20. VC Asshat Move #1

by David Cohen of Techstars 

Beware of competitive dynamics when you raise. There are plenty of bad actors out there. David Cohen puts it eloquently in this post.

21. Fatal Pinch

by Paul Graham of Y-Combinator

Got 6 months or less in the bank? You are running out of money and it is not a great place to be in. Actually it is much worse than you think. Read this dark and sober post by Paul Graham to find out what your real options are.

22. Three Questions For Startups To Answer For Themselves In A Volatile Fundraising Environment

by Tomasz Tunguz of Redpoint Ventures

When Winter is here, how do you think about capital and financing of your startup? Read this excellent, short post by Tomasz.

23. Drink When Served

by Mark Solon of Techstars

Should you raise more or less capital? Mark Solon, Managing Partner at Techstars argues that it makes sense to raise more capital if available. Given current cool climate and series A crunch this is a sage advice.  Also read my post on this topic – Why it makes sense to raise more capital when you can.

24. What Seed Funding Boom Means for Raising Series A

by Josh Kopelman of First Round Capital

Raising Series A is a lot harder than raising a seed round. Seed capital is abundant, while series A bar is really high. In this awesome, nuanced post Josh Kopelman, Founding Partner of First Round Capital gives the founders advice on how to think about the Series A funding landscape.

25. The Babe Ruth Effect in Venture Capital

by Chris Dixon of A16Z

Why do VCs obsess with Unicorns? How do VCs make money, anyway? Chris illuminates the rise of large funds and the dynamic of venture capital and puts it in a simple and accessible form. This post is likely to bring you closer to understanding why VCs say NO to so many opportunities.


What are your favorite posts on fundraising? Please share with us and we will update the post in coming weeks.