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TROYHENIKOFF

From the MATH Collective

Startup Lessons from decades of
real life experience from Troy Henikoff

Videos, articles and insights meant to showcase founders' journeys and help you grow with greater certainty. 57 lessons, 4 hours, every second searchable.

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I'm about to raise My pricing feels wrong I need a financial model What's my CAC really? Customers keep leaving Splitting equity Note or priced round? My pitch isn't landing
Lessons
57
Videos
58
Hours
4
Searchable moments
2,633

Being A Better Entrepreneur

34 lessons

Structuring your business for success

  1. 2:52 Founders, Allocating Equity and Avoiding the BIG Mistake We've talked about convertible debt, SAFE, equity, all kinds of structures. But what we failed to do is talk... May 2019
  2. 4:41 Founder Vesting, RSU’s and 83(b) Elections – Making Sense of the Mess Last week we talked about the importance of a founders agreement when you have more than one founder. Jun 2019

From the trenches — tricks to operate better

  1. 5:44 Don’t trust Google for your customer retention metrics At MATH, we talk a lot about early customer signals. You see, we want to see that a company is going to be... Mar 2022
  2. 2:46 How Defining Purpose Yields Results Any of you who've been to my open office hours have seen this firsthand because most likely the first words out... Dec 2021
  3. 5:19 How to Learn from Churn So, I was in a board meeting today and when the slide came up that described what was going on in churn, one of... May 2021
  4. 3:48 The Right KPIs Matter It's not just because our firm name is MATH Venture Partners. You see, it's because we believe the companies... May 2021
  5. 1:59 Levers: The Framework for Building Repeatability into Your Business This morning I'm here to announce something new. Well, actually a little old, old school. Apr 2021
  6. 3:42 What Makes a Truly GREAT Entrepreneur? The other day I was teaching at the Kellogg School at Northwestern and a student asked me, Hey Troy, what do... Mar 2019
  7. 2:58 How to Get Better Introductions As a VC, I meet with hundreds and thousands of entrepreneurs every year. And one of the most common things they... Jan 2021
  8. 2:14 3 Things You Need to Have a Successful Business For those of you who know me well, you know that I love cycling. And in cycling, there's an adage. The three... Jan 2020
  9. 2:44 Reading Between the Lines We've talked about cadence and expectation setting and all those things are great. And what you say is so... Mar 2020
  10. 4:27 Paying for Services with Equity In the last couple of weeks, I've had the same question asked multiple times. Seems like a great opportunity to... Feb 2020
  11. 2:40 How to Make Your Annual Budget Twice as Valuable As an entrepreneur, everything you do should be a twofer. By that I mean, number one, it should move your... Jan 2020
  12. 2:07 How to Find the Right Job at the Right Start Up People come to me and say, hey, what company should I work for? Where should I find the right fit? And I give... Dec 2019
  13. 2:09 The Entrepreneur’s “Wheel of Fortune” In many cases, you've heard me talk about focus and how important focus is for entrepreneurs. As a matter of... Nov 2019
  14. 3:09 Mistakes Entrepreneurs Make Setting Prices Today I want to talk about one of the biggest mistakes that I see entrepreneurs making and that is pricing. Feb 2019
  15. 3:24 How to Optimize Use of Capital In the last few weeks, I've had the same question from a handful of entrepreneurs. And it's basically, so I... Mar 2019
  16. 3:26 Your Baby is Ugly! It's something we've talked about before and frankly we're going to talk about again because it's something I... Jun 2019
  17. 2:47 The Equity Conversation This week I got a phone call from one of our founders and it was similar to phone calls I get almost every... Sep 2019
  18. 3:18 Communicating to Your Investors – It’s More Important Than You Think… Much of being a great entrepreneur is about being a great communicator. As a leader of a company, you have to... Oct 2019

Customer Acquisition Cost and Lifetime Value — the fundamentals

  1. 4:33 Why is Troy Obsessed with CAC? If you've ever been in a meeting with me, you've probably heard me dig in on customer acquisition cost or CAC.... Apr 2019
  2. 2:10 Pain Killer vs. Vitamin I can't believe that we've been doing these videos for a little over a year and we haven't touched on one of my... Dec 2019
  3. 4:43 How to Answer the Question – What is your CAC? Last week we talked about lifetime value customer acquisition cost and the ratio of LTV to CAC and specifically... May 2019
  4. 3:33 Decoding the Revenue Puzzle All right, this week we're going to take a break from financial modeling to talk about revenue, that big number... Aug 2019

Financial Modeling

  1. 5:47 Financial Modeling Part 1 – What is a Financial Model? You see, one of the talks that I give that is most popular around the Techstars network is about financial... Jul 2019
  2. 6:16 Financial Modeling Part 2 – The Power of a Financial Model Last time when we started talking about financial modeling, we explained a few concepts. The first is that a... Jul 2019
  3. 5:45 Financial Modeling Part 3 – Modeling Your Expenses We used the financial model to understand the impact of raising prices and what happens when customers churn... Aug 2019
  4. 4:52 Financial Modeling Part 4 – How Fundraising and Dilution Impacts YOUR Equity as a Founder The last time we talked about financial modeling, we came to the conclusion that spending more money in... Aug 2019
  5. 2:20 Financial Modeling Part 5 – Modeling Financial Growth We've been talking about financial modeling the last few videos and there's some confusion about how to model... Sep 2019
  6. 2:08 Do You KNOW the Difference between Gross Profit and Contribution Margin? Today we're going to talk about the difference between gross profit and contribution margin. Two terms that are... Nov 2019
  7. Startup Financial Modeling, Part 1: What is a Financial Model? This article was originally published over on Startup Rocket here , and written by Will Little and Troy Henikoff. Sep 2016
  8. Startup Financial Modeling, Part 2: Start with Your Assumptions This article was originally posted on Startup Rocket here , and written by Will Little and Troy Henikoff. Oct 2016
  9. Startup Financial Modeling, Part 3: The Income Statement and Custom Detail Tabs This article was originally posted on Startup Rocket here , and written by Will Little and Troy Henikoff. Oct 2016
  10. Startup Financial Modeling, Part 4: The Balance Sheet, Cash Flow and Unit Economics This article was originally published over at Startup Rocket here , and written by Will Little and Troy Henikoff. Oct 2016

Fundraising

19 lessons

Fundraising — when and how much

  1. 2:45 What are investors REALLY thinking about when they ask about your CAC…? LTV and CAC. We have talked about these many times in these videos and I'm going to do it again. And not just... Jun 2022
  2. 2:50 Raise for Outcomes, Not Headlines It has never been a better time to be an entrepreneur. We are all seeing our friends raise great amounts of... Oct 2021
  3. 3:47 Think twice before committing to strategic investors In the last two weeks, I have had three entrepreneurs come to me all excited about the opportunity they have. May 2022
  4. 4:24 Friction Kills Deals Today, we're going to talk about deals and specifically, I want to talk about getting deals done. Mar 2021
  5. 2:36 Funding the Valley Here's how I think about it. This is your company, time, and the value that you create. Generally, most... Nov 2018
  6. 2:51 When to Raise Capital Hi, I got a lot of great feedback from last week's video on crossing the chasm, how to get across that valley of death. Nov 2018
  7. 4:45 Impact of Raising Too Much The last couple of weeks we've been talking about fundraising and entrepreneurs get so excited when it comes to... Nov 2018
  8. 3:06 Our Business is a Relationship Business Our business is a relationship business. And when I say our business, I mean both investors and entrepreneurs. Feb 2020

Pitching Investors

  1. 3:15 Don’t Send the Deck A question I've gotten for years from entrepreneurs is what do I do when an investor I haven't met says send me... Jun 2021
  2. 3:21 How to Get Great Investor Meetings Hi, I'm here today to share with you one of my favorite fundraising hacks. You've probably heard the expression... Apr 2021
  3. 4:00 Finding the Right Investor One of the most common things that I heard was we've been talking about how we construct these decks and how we... Dec 2018
  4. 3:27 Pot of Gold A lot of people have written blog posts on how to create the perfect fundraising deck. The right 10 slide deck,... Dec 2018
  5. 7:23 3 Passes on How to Make a Better Pitch For years, I have been coaching and mentoring entrepreneurs. And every year, we get dozens and dozens, hundreds... Oct 2023
  6. 3:17 The Secret of the Ask Thank you for all of you who have been watching the videos and sending me questions and comments. It's been... Dec 2018

Structuring your financing round

  1. 4:34 Back to Basics- Valuations, Option Pools and What You Need to Know Before Raising Capital All right, I am still surprised at how many entrepreneurs are confused about pre-money valuation, post-money... Oct 2019
  2. 4:16 Convertible Debt/SAFE vs. Equity I hope everybody had a great holiday season and is geared up for this new year. And because it's the first of... Jan 2019
  3. 4:37 The Rule of Two Last time we were talking about how convertible debt and SAFEs compare to equity when it comes to fundraising.... Jan 2019
  4. 2:43 A Twist on Convertible Notes Last week we talked about convertible debt and how important it is to think one or two moves ahead. I have one... Jan 2019
  5. 3:32 WAIT – Now Troy Likes Convertible Notes? In all of my ranting about the problems of convertible debt and SAFE notes, I left many people with the... Feb 2019

Latest

interview Tech Scenes Unplugged with Troy Henikoff, Managing Director of Math Venture Partners In this episode of Tech Scenes Unplugged, Jeff Martin reconnects with Troy Henikoff. December 4, 2024 7:23 lesson 3 Passes on How to Make a Better Pitch For years, I have been coaching and mentoring entrepreneurs. And every year, we get dozens and dozens, hundreds and... October 12, 2023 essay Angel Investing 101 In this recording Troy Henikoff and Chris Deutsch discuss the basics of angel investing. June 27, 2023 essay Table of contents Being a better entrepreneur Structuring your business for success Allocating founders’ equity and avoiding a BIG... June 26, 2023 essay The Future of MATH Today, we are publicly announcing that MATH will not raise a third fund. In MATH I, we proved our thesis that... July 19, 2022 essay Nailing cold investor outreach Venture firms live for deal flow. The more founders we meet, the more opportunities we have to find the few founders... June 23, 2022