

High Bit
Initialized Capital
Welcome to High Bit, a podcast hosted by Initialized Capital managing partner Brett Gibson about the art of technical problem-solving.
A high bit is the most significant part of the binary representation of a number. In programming language, it is commonly referred to as the most important thing you need to understand about a problem.
We spoke with our guests about just that. In each episode, we’ll break down a gnarly engineering problem and hear how the builder’s ingenuity and inventiveness led to a successful outcome.
A high bit is the most significant part of the binary representation of a number. In programming language, it is commonly referred to as the most important thing you need to understand about a problem.
We spoke with our guests about just that. In each episode, we’ll break down a gnarly engineering problem and hear how the builder’s ingenuity and inventiveness led to a successful outcome.
Episodes
Mentioned books

Jun 21, 2024 • 21min
Developing a Proprietary Logistics System for a Consumer Brand With Jenny Fleiss
In this episode of "High Bit," Initialized partner and Rent the Runway co-founder Jenny Fleiss discusses how she developed a proprietary logistics system for a consumer brand. Jenny opens up about the early challenges faced in starting Rent the Runway, the strategic decisions made in scaling a complex operation, and how she built an in-house logistics team.
CHAPTERS
00:00 Introduction
1:45 Jenny's transition to investing and current areas of investing interests at Initialized.
4:38 The initial logistics challenges at Rent the Runway.
6:36 Partnering with local dry cleaners and scaling operations.
9:01 Building a proprietary logistics system from scratch.
13:00 Key takeaways from managing and scaling a complex logistics operation.

May 15, 2024 • 28min
Integrating LLMs in Robotic Process Automation With Automat’s Gautam Bose
In this episode of "High Bit," Automat founder and CTO Gautam Bose talked about the challenges of working with LLMs in robotic process automation, and the importance of rigorous testing procedures.
CHAPTERS
00:00 Introduction
01:30 What Automat Does and How They Started
03:06 Challenges in Building RPA
08:46 What the Future of RPA Looks Like
12:52 How Automat Ensures Reliability in Its LLMs
14:53 Automating Complex Workflows With Robust SOP Collections
20:17 Coming Up With Solutions to Complex Orders
23:41 Improving Ideas Through Iteration

May 15, 2024 • 32min
Making Blockchain Technology Accessible With Horizon’s Peter Kieltyka
In this episode of "High Bit," Peter Kieltyka discusses the dual challenge of maintaining decentralization and accessibility in blockchain technology, and the growing significance of APIs in building connected systems.
CHAPTERS
00:00 Introduction
01:38 What Horizon Does and the Challenges in Delivering the Crypto Gaming Platform
04:53 How Peter Came to the Decision of Working on Blockchains
07:07 How APIs Are Created for Modern Client Server Web Applications
12:25 All About GRPC
15:40 Chi: Peter’s Software That Lets You Write Microservices
21:15 Peter’s 2 Favorite Books He Recommends to Everyone He Works With
27:27 What Else to Look Forward To from Horizon

Jan 28, 2024 • 30min
Building a Developer-Focused Public Cloud with Fly.io CEO
In this episode of "High Bit," Brett Gibson chats with Kurt Mackey, CEO of Fly.io, to break down how they challenge big cloud providers, overcome global logistical nightmares, and continuously evolve their software stack. From hardware setup challenges to growth-driven solutions, Kurt explains the highs and lows of managing a developer-focused public cloud.
00:00 Introduction
1:21 Starting off with what Fly.io is
3:26 Zooming in on the developer experience
6:19 What Fly.io’s journey was like
19:23 Key takeaways from setting up the public cloud globally
25:20 What we can expect from the developer-facing stack trend

Jan 28, 2024 • 32min
Navigating the Frontier of Safer Financial Systems with TRM's Rahul Raina
In this episode of "High Bit," host Brett Gibson interviews Rahul Raina, cofounder and CTO of TRM Labs. Rahul shares insights into TRM's mission of creating a safer financial system and discusses the launch of their innovative features. The conversation delves into Rahul's background, TRM's approach to tackling financial crimes, and the challenges of processing massive amounts of data in the ever-evolving world of crypto.
00:00 Introduction
2:09 TRM’s mission to build a safer financial system
9:20 The question that started TRM
14:47 Breaking down their iteration process
20:21 The journey to pushing the state of the art
24:52 Proportionality as update strategy

Jan 28, 2024 • 33min
Scaling AI Agents for Real-World Tasks with Parcha CEO AJ Asver
In this episode of "High Bit," AJ Asver, CEO of Parcha, discusses the challenges of building AI agents for complex tasks. Parcha's AI agents automate operations and compliance, addressing the gap between proof of concept and production.
00:00 Introduction
01:51 Introducing Parcha and what they do
4:02 Breaking down how an AI agent relates to LLM
12:53 The challenges in scaling AI agents
17:15 Making the system as accurate as possible
28:51 Predicting the rise of verticalized agents

Jun 22, 2023 • 43min
Building Blockchain Infrastructure With Aaron Henshaw of Bison Trails
In this episode of High Bit, Aaron discusses the challenges of hiring a team to build an infrastructure-as-a-service platform for blockchain networks. When Aaron and his cofounder Joe Lallouz first created Bison Trails, they initially faced challenges running nodes and infrastructure for different networks. They found that by investing in tests early on and improving automation capabilities, they could streamline operations. Coinbase eventually acquired Bison Trails in January 2021.
For more info on High Bit, and to listen to all of the other episodes, visit: www.Initialized.com/HighBit
Topics:
2:28 Aaron's Background and How He Became an Engineer
5:21 Building Grand St. and Selling the Company to Etsy
10:55 The Early Days of Building Bison Trails
16:21 Building the Early Team of Infrastructure Engineers with Blockchain Experience
19:53 Slashing: The Penalties Imposed on Validators in Blockchain Networks for Misbehavior
27:07 What Bison Trails Taught Aaron About Building Large Organizations
33:28 Aaron on Lessons He Learned While Hiring the Bison Trails Team
38:00 Life After Bison Trails and Coinbase. What's Next for Aaron Henshaw?
High Bit is a new podcast hosted by Initialized Capital managing partner Brett Gibson about the art of technical problem-solving.
A high bit is the most significant part of the binary representation of a number. In programming language, it is commonly referred to as the most important thing you need to understand about a problem.
We spoke with our first four guests about just that. In each episode, we’ll break down a gnarly engineering problem and hear how the builder’s ingenuity and inventiveness led to a successful outcome.
High Bit is produced by Initialized Capital and hosted by Brett Gibson. Our showrunner is Candy Cheng. Episodes were shot and edited by Jordan Berns. Production support by Kevin Heinz and BTB Video Production.

Jun 22, 2023 • 31min
Troubleshooting Space Engineering with AstroForge’s Jose Acain
In this episode of High Bit, Jose walks us through the challenges of troubleshooting a complex problem encountered during the pre-launch testing of a space-bound asteroid mining refinery. Using a real-life example, he illustrates the application of a fishbone diagram and the necessity of methodical problem-solving, even under extreme time pressure.
Topics:
1:41 What is AstroForge?
7:13 How Jose Met His Cofounder Matt Gialich
13:18 Using a Fishbone Diagram to Find the Root Cause of a Problem
15:01 The "Holy Shit" Moment When a Launch Does Not Go According to Plan
20:37 Validating All the Points of Failure to Get to a Solution
26:25 Lessons Learned from Working Under Time Pressure
High Bit is a new podcast hosted by Initialized Capital managing partner Brett Gibson about the art of technical problem-solving.
A high bit is the most significant part of the binary representation of a number. In programming language, it is commonly referred to as the most important thing you need to understand about a problem.
We spoke with our first four guests about just that. In each episode, we’ll break down a gnarly engineering problem and hear how the builder’s ingenuity and inventiveness led to a successful outcome.
High Bit is produced by Initialized Capital and hosted by Brett Gibson. Our showrunner is Candy Cheng. Episodes were shot and edited by Jordan Berns. Production support by Kevin Heinz and BTB Video Production.

Jun 22, 2023 • 32min
Unlocking Crypto Trading Efficiency With Talos CTO Ethan Feldman
In this episode of High Bit, Ethan reveals the unique challenges of building a reliable and global crypto trading platform. “There’s no downtime because crypto trades 24/7,” he said. “So in that way, it’s a lot more like Google than the New York Stock Exchanges.”
Ethan also shared the art of balancing safety and speed in product development. “You need to adapt, and you need to change up your workflow as the market changes. We want to wrap that whole messy ecosystem in a layer that allows institutions to interact with crypto just like they would any other asset class.”
Topics:
02:26 From Broadway Technology to Talos
06:23 Crypto Trading is "More Like Google Than NYSE"
11:46 Examining the Various Failure Scenarios of Trading Crypto
15:56 The Importance of Getting Details Correct in Making a Successful Trading System Work
21:35 Client Communication as Part of the Engineering Effort
25:05 Building Safety Features into the Product
29:30 Adaptability Around Messiness
High Bit is a new podcast hosted by Initialized Capital managing partner Brett Gibson about the art of technical problem-solving.
A high bit is the most significant part of the binary representation of a number. In programming language, it is commonly referred to as the most important thing you need to understand about a problem.
We spoke with our first four guests about just that. In each episode, we’ll break down a gnarly engineering problem and hear how the builder’s ingenuity and inventiveness led to a successful outcome.
High Bit is produced by Initialized Capital and hosted by Brett Gibson. Our showrunner is Candy Cheng. Episodes were shot and edited by Jordan Berns. Production support by Kevin Heinz and BTB Video Production.

Jun 22, 2023 • 24min
The Future of Nail Care Using AI & Robotics with Clockwork’s Renuka Apte
In this episode of High Bit, Renuka shares the evolution of Clockwork’s AI-powered nail-painting robot. She shares her insights into safe AI utilization and how she adopted software engineering principles into the hardware process.
Topics:
1:56: Renuka’s Background as a Systems Engineer at Nvidia
5:27: Using an Off-The-Shelf AI Model to Create the First Version of Clockwork
10:06: Discovering Pointillism in Nail Painting
14:46: Using AI in Safe Ways
18:29: A Very Humbling Lesson for a Software Engineer
22:55: Making Nail Painting as Easy as Grabbing a Cup of Coffee
High Bit is a new podcast hosted by Initialized Capital managing partner Brett Gibson about the art of technical problem-solving.
A high bit is the most significant part of the binary representation of a number. In programming language, it is commonly referred to as the most important thing you need to understand about a problem.
We spoke with our first four guests about just that. In each episode, we’ll break down a gnarly engineering problem and hear how the builder’s ingenuity and inventiveness led to a successful outcome.
High Bit is produced by Initialized Capital and hosted by Brett Gibson. Our showrunner is Candy Cheng. Episodes were shot and edited by Jordan Berns. Production support by Kevin Heinz and BTB Video Production.


