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Everything on the site, newest first. 81 pieces.

1. 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
2. 7:23
   lesson 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 and hundreds...
   Mark Achler October 12, 2023
3. essay
   Angel Investing 101
   In this recording Troy Henikoff and Chris Deutsch discuss the basics of angel investing.
   June 27, 2023
4. essay
   Table of contents
   Being a better entrepreneur Structuring your business for success Allocating founders’ equity and avoiding a BIG mistake...
   June 26, 2023
5. 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 companies with...
   July 19, 2022
6. 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 we invest...
   June 23, 2022
7. 2:45
   lesson 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 because I like...
   June 2, 2022
8. essay
   Channel Partnerships Part II: Engaging and Closing Partners
   This is part 2 in a series on channel partnerships. You can read part 1 here . Channel partnerships can 10x your customer...
   May 12, 2022
9. 3:47
   lesson 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 10, 2022
10. essay
    Channel Partnerships Part I: Building an ideal profile and selecting the best
    This is part 1 in a series on channel partnerships.
    May 5, 2022
11. essay
    The Easiest Way to Impress Your Future Investors: The Early Stage Data Room
    ” We see a ton of data rooms at MATH as investors. Sometimes it’s to support our existing portfolio as a sanity check and most...
    April 14, 2022
12. 5:44
    lesson 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 successful before...
    March 24, 2022
13. essay
    The most effective way to do investor updates
    In the past, when I met founders who were not disciplined with their investor communications, I typically forwarded them this...
    March 14, 2022
14. essay
    Stop selling yourself short: Your market size is bigger than you think!
    As an early stage investor, I look at two elements: credible founders & a massive potential market. You most likely have a...
    March 9, 2022
15. 2:46
    lesson 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 of my mouth...
    December 21, 2021
16. essay
    Use Superfounders to Accelerate Fundraising
    One of my favorite founders in the world is Jeff Kahn from Rise Science . He and his partner Leon have been steadily working...
    November 3, 2021
17. 2:50
    lesson 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 money at awesome...
    October 20, 2021
18. interview
    Chicago Capital Podcast: Troy Henikoff on Ted Lasso, VC, and Building a Winning Team
    MATH Partner Troy Henikoff is featured on the Chicago Ventures Podcast.
    October 1, 2021
19. 4:23
    lesson 4:23
    Higher Valuations Are Not Always Better
    A high valuation feels like winning. The round after it is where you find out.
    September 15, 2021
20. 3:15
    lesson 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 the deck I'll...
    June 29, 2021
21. 5:19
    lesson 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 the other...
    May 20, 2021
22. 3:48
    lesson 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 that are metrics...
    May 5, 2021
23. 1:59
    lesson 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.
    April 20, 2021
24. 3:21
    lesson 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 that investors...
    April 6, 2021
25. 4:24
    lesson 4:24
    Friction Kills Deals
    Today, we're going to talk about deals and specifically, I want to talk about getting deals done.
    March 9, 2021
26. 2:58
    lesson 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 ask me for is...
    January 26, 2021
27. essay
    Entrepreneurship, fundraising, and practical advice for startup founders
    Originally published by Will Little Will Little , a bioengineer turned software developer and now venture builder/investor at...
    October 14, 2020
28. 2:44
    lesson 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 important. But...
    March 12, 2020
29. 3:06
    lesson 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.
    February 27, 2020
30. 4:27
    lesson 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 do a video.
    February 11, 2020
31. 2:14
    lesson 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 things you really...
    January 30, 2020
32. 23:55
    lesson 23:55
    The Inevitable Economics of Trust
    Trust is a muscle, not a mood — and whether you build it eventually shows up in the numbers.
    Mark Achler January 17, 2020
33. 2:40
    lesson 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 business forward and...
    January 16, 2020
34. 2:07
    lesson 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 them two pieces...
    December 19, 2019
35. 2:10
    lesson 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 favorite topics.
    December 5, 2019
36. 2:08
    lesson 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 very similar...
    November 21, 2019
37. 2:09
    lesson 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 fact, you've...
    November 14, 2019
38. 4:34
    lesson 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 valuation, option...
    October 24, 2019
39. 3:18
    lesson 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 effectively...
    October 10, 2019
40. 2:47
    lesson 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 week. She had an...
    September 26, 2019
41. 2:20
    lesson 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 growth in your company.
    September 12, 2019
42. 4:52
    lesson 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 customer acquisition...
    August 29, 2019
43. 5:45
    lesson 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 faster because...
    August 15, 2019
44. 3:33
    lesson 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 on the top of...
    August 1, 2019
45. 6:16
    lesson 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 financial model...
    July 18, 2019
46. 5:47
    lesson 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 modeling and how to...
    July 2, 2019
47. 3:26
    lesson 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 believe is so...
    June 20, 2019
48. 4:15
    lesson 4:15
    Not All Revenue Is Created Equal
    Investors prefer recurring revenue over services. Following that as a rule can cost you customers.
    Mark Achler June 12, 2019
49. 4:41
    lesson 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.
    June 6, 2019
50. 2:52
    lesson 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 about what kind...
    May 22, 2019
51. 4:43
    lesson 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 how important...
    May 9, 2019
52. interview
    Tech Scenes Chicago with Troy Henikoff
    Get to know Troy Henikoff on Lead by Change’s latest episode of Tech Scenes. Learn about how MATH Venture Partners got...
    May 6, 2019
53. essay
    Setting the Record Straight
    ” On the one hand, this is good. We worked with Crain’s to receive media coverage for the successful closing of our second...
    May 2, 2019
54. 4:33
    lesson 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. Why am I so...
    April 10, 2019
55. 3:42
    lesson 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 you think makes a...
    March 28, 2019
56. 3:24
    lesson 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 worked hard and I...
    March 14, 2019
57. 3:32
    lesson 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 impression that they...
    February 28, 2019
58. 3:09
    lesson 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.
    February 14, 2019
59. 2:43
    lesson 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 more piece I...
    January 31, 2019
60. 4:37
    lesson 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. And a bunch of...
    January 17, 2019
61. 4:16
    lesson 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 the year, we'll...
    January 3, 2019
62. 4:00
    lesson 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 build a great...
    December 20, 2018
63. 3:17
    lesson 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 amazing and it...
    December 13, 2018
64. 3:27
    lesson 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, the right 20...
    December 6, 2018
65. 4:45
    lesson 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 fundraising....
    November 29, 2018
66. 2:51
    lesson 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.
    November 15, 2018
67. 2:36
    lesson 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 startups follow a...
    November 6, 2018
68. interview
    Bootstrapping in America with Troy Henikoff
    Co-founder & Managing Director, Troy Henikoff talks about his entrepreneurial path and MATH Venture Partners with Kristi Ross...
    May 31, 2018
69. essay
    Which Chicagoans are best at mentoring women?
    com and co-founder of Excelerate Labs, now Techstars Chicago. ” Henikoff requires chemistry in a mentoring relationship.
    November 13, 2017
70. essay
    The New York Times Test
    ” He declared his expectation that anything he said, wrote or did could end up in the New York Times one day, and he used that...
    July 5, 2017
71. interview
    The Distance Podcast: Troy Henikoff
    Troy Henikoff was a college student in 1984 when he wrote his first program, a piece of software to help his grandfather’s...
    July 5, 2017
72. interview
    Q&A with Troy Henikoff: Are Entrepreneurs Born or Made?
    This article was originally published on Salesforce, and written by Laura Norman.
    April 6, 2017
73. lesson
    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.
    October 7, 2016
74. lesson
    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.
    October 2, 2016
75. lesson
    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.
    October 2, 2016
76. lesson
    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.
    September 15, 2016
77. essay
    Startup Stories: Nothing Matters More Than Your Customers.
    Troy Henikoff, Managing Director of MATH Venture Partners and Techstars has so much knowledge to add. He sat down with Trish...
    June 25, 2016
78. interview
    Techstars Conversation with Troy Henikoff
    IF YOU’RE A BUDDING CHICAGO STARTUP, THEN THIS EPISODE IS FOR YOU – WE’VE GOT TECHSTARS CHICAGO MANAGING DIRECTOR TROY...
    November 5, 2015
79. interview
    Troy Henikoff Interview on Growth Hacker
    Troy Henikoff is the Managing Director of Techstars Chicago, and before that he was the founder and president of a $100M exit.
    August 27, 2015
80. essay
    Troy Henikoff makes list of Top 50 Chicagoans in Tech
    Here are 50 people you should know if you care about Chicago tech. They’re the ones to call if you’re trying to launch an...
    July 24, 2015
81. essay
    Q: What are some common questions asked by VCs during a first pitch meeting?
    A: At MATH Venture Partners we’re focused on customer acquisition and so most of what we ask during these meetings is to learn...
    December 8, 2014

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