What we covered:

– As Math Academy has grown over the past year, we're getting a better sense of general do's and don'ts when scaling a startup. We've learned hard lessons about overloading the database, the task processor, and our team, requiring numerous infrastructure and process updates.

– Schools have been using the system and we've built plenty of additional features to, among other things, accommodate unique billing schemes and make it easy for teachers to manage classes on the system.

– We've intentionally grown organically and were self-funded, which forced us to do things manually at the beginning. Years ago, we taught math classes in person and Jason onboarded our first online users on hundreds of hour-long individuals and calls. These were crucial experiences to learn who our customers are, what they want from the product, and common failure modes.

– In our experience, doing things manually at the beginning ensures that you 1) build a product that customers actually get value from, and 2) you don't clutter your product with unnecessary bells and whistles that don't add value. In other words, you have to do the manual work to earn the right to scale.

Outline:

0:00 - Introduction

2:18 - Building infrastructure to handle increasing load

3:41 - Bringing on AWS expertise to robustify the backend

4:22 - An overloaded database enters a new realm of physics

5:50 - Prioritizing execution over perfection in start-ups

6:33 - Paying the bill for accumulated infrastructure debt

7:53 - Improving job prioritization of the task processor

9:52 - Benefits of scaling organically

11:42 - Wisdom is the result of failures

12:18 - There is no substitute for experience

13:17 - Focusing on solving problems, not advertising

14:48 - Upgrading with surgical precision

15:35 - The pain-point compass

17:04 - Managing finite time and resources

18:27 - Development of the gravity feature

20:42 - Gravity is a suggestion, not a hard override

22:25 - Limiting gravity to avoid cognitive overload

28:29 - Balancing customization and customer confusion

31:28 - The feature sandbox

33:58 - Increasing volume of customer support emails

35:22 - Additional infrastructure requirements for schools

36:18 - Learning about the customer through direct interaction

38:14 - Step 1: Manually added schools using spreadsheets

40:22 - Step 2: Developed tools to handle specialized school requests

41:23 - Step 3: Goal is 100% self-service sign-ups for schools

42:32 - Solve the problem manually first, then automate it

43:44 - Why focus on schools?

46:15 - Math Academy goes to college

49:37 - You can’t anticipate every edge case

52:14 - Letting user behavior build the product roadmap

58:54 - Becoming successful means working harder

1:00:24 - The customer support hurdle

1:03:27 - How Justin’s expanding roles drove growth (both personal & company)

1:09:03 - Teaching as market research for Math Academy

1:10:52 - The value of having been inside the trade

Follow on X:

Math Academy - https://x.com/_MathAcademy_

Justin Skycak - https://x.com/justinskycak

Jason Roberts - https://x.com/exojason