On The Frontier

For anyone interested in developer tooling, you won’t be able to find better analysis than the Redmonk team and this pod goes in depth into trends, analysis, and AI’s impact on coding.

James Governor and Kate Holterhoff are analysts at Redmonk, the developer focused analyst firm. They have been doing analysis of open source tooling and developer trends since 2002 when the firm was founded (20+ years ago). In this episode, we talk about analyzing what will persist in hype cycles, AI’s impact on coding practices & languages, and how not to extrapolate our biases in outcomes onto data. If you are a fan of dev tools and open source, you will love this conversation as you can’t find two people who spend more time thinking about this area than James and Kate along with the rest of the Redmonk team.

Where to Find Redmonk:

·       James’ Twitter: https://twitter.com/monkchips

·       Kate’s Twitter: https://twitter.com/KateHolterhoff

·       James’ LinkedIn: https://www.linkedin.com/in/jamesgovernor/

·       Kate’s LinkedIn: https://www.linkedin.com/in/kateholterhoff/

·       Redmonk’s Blog: https://redmonk.com/ 

·       Redmonk’s Podcast: https://redmonk.com/blog/2023/12/07/the-monkcast/ 

Where to Find Shomik:

·       Twitter: https://twitter.com/shomikghosh21

·       LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

·       Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(00:48) – Founding Redmonk Alongside the Rise of Open Source

(03:39) – How Redmonk Analyzes Products

(06:58) – Diagnosing What’s Real in Tech Hype Cycles

(15:56) – Is AI Having a Large Impact on Language Rankings?

(25:50) – Downstream Impact of Having AI Generate Majority of Code

(29:45) – Impact of Agents Managing Code Bases

(34:10) – Rise of Frontend Tooling (Again)

(40:09) – Thoughts on Open Source License Changes in Prominent Projects

(44:40) – New Analysis & Events Coming up for Redmonk

Show Notes:

-       Frontend Developers are the New Kingmakers

-       What’s Going on With Language Rankings

-       AI: The Difference Between Open and Open Source

How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube

All of us as knowledge workers are interested in improving our time management. This episode is packed with tips from a founder who breathes this with the product everyday.

Matt Martin is the Co-Founder & CEO of Clockwise and previously an Eng Manager at Salesforce through the RelateIQ acquisition. In this episode, we discuss time management tips and calendar optimization. We dive into research behind different aspects of time and behavioral management. And of course, get Matt’s insights from 7+ years of building a rapidly growing SaaS app.

Where to Find Matt:

·       Twitter: https://twitter.com/voxmatt

·       LinkedIn: https://www.linkedin.com/in/voxmatt/

Where to Find Shomik:

·       Twitter: https://twitter.com/shomikghosh21

·       LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

·       Newsletter: https://www.shomik.substack.com

·       Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(01:36) – Overview of Clockwise

(02:50) – Why is Software Useful for Calendar Management

(05:21) – Technical & Behavioral Aspects to Tackle Around Calendars

(10:40) – Balancing Single Player & Multi-Player Use Cases and Motions

(16:00) – Package & Pricing Between Single & Multi-Player

(17:57) – Do Things That Don’t Scale Moment

(22:13) – Lack of Intentionality in Time Management

(23:55) – Importance of Breaks in Back to Back Meetings World

(26:15) – “Attention Residue” (aka context switching latency)

(29:22) – Personalization of Time Management

(32:06) – Weekly Look Ahead Emails Instead of Calendar Audits

(35:15) – Team Discussions Around Optimal Personalized Work Schedules

(37:55) – Software Eng Meeting Benchmark Report Results

(40:40) – Cleaning Slate on Standing Meetings

(41:42) – AI Scheduling

Show Notes:

-       Research on “Attention Residue”

-       Clockwise’s Software Engineering Meeting Benchmark Report

-       AI Scheduler by Clockwise

How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube

As much as we talk about company building and technology trends on this podcast, one of the most essential aspects of entrepreneurship is maintaining your health. High performance comes first form taking care of your body, mind, and lifestyle to drive clear decision making.

Ben Canning is the Founder of We Hack Health and a trainer to founders & employees across the tech and cybersecurity ecosystem. He has coached many high performers in their jobs and helped them improve even further by focusing on their health. In this episode, we talk about common concerns and blockers that Ben sees amongst various clients. We dive into the four pillars of health (Sleep, Mental Health, Nutrition, and Fitness) and Ben’s basic tactics to approach each of them in a sustainable manner. Ben provides a tactical roadmap to how to approach a sustainable healthy lifestyle and how so much relies on having a mindset to continue to do hard things.

Where to Find Ben:

· Twitter: https://twitter.com/bencanning87

· Podcast: https://wehack.health/

Where to Find Shomik:

· Twitter: https://twitter.com/shomikghosh21

· LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

· Newsletter: https://www.shomik.substack.com

· Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(01:42) – Where Should People Start On Their Health Journey

(03:10) – Habit Formation

(04:20) – Making Time for Health

(06:05) – Your Future Self

(09:23) - Identifying Your Drive to Make Change

(15:40) - Defining Daily Non-Negotiables

(17:10) - Managing Health as a Parent

(20:38) - Mindset

(26:58) - Sleep & Supplementation 101

(35:09) - Exercise 101

(44:45) - Nutrition 101

(54:13) - Go All-In to Achieve Results

(55:35) - Ben & Dave’s New Supplements Company - Zero Day!

Show Notes:

- Resources to Reach Ben and his Training

How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube

Given all that’s happened in the year since this first aired (March 2023), replaying this for everyone to understand what is happening within the Semiconductor space, the different players, why Nvidia is set up to dominate (Doug predicted this well before that 1st epic quarter), and much more. Since this episode aired, Nvidia is up 2.6x!

Doug O’Laughlin is the Founder of Fabricated Knowledge, one of the largest technology newsletters on Substack, covering the semiconductor industry. Many may know Doug from his anonymous Twitter. He joins us today to dive deep into the semiconductor industry. Doug takes an immensely complex industry in semis and distills everything down into digestible analogies regarding semiconductor manufacturing and the actual chips themselves. Doug specifically addresses how certain semi industry areas have significant moats, how the rise of LLMs is all linked to more chips being used, what public companies are well-positioned for the future of semis. Simply put, this is the best explainer I’ve ever heard or read about the semiconductor industry to understand what’s powering all the applications and devices we use daily under the hood.

Where to Find Doug:

* LinkedIn: https://www.linkedin.com/in/dougolaughlin/

* Twitter: https://twitter.com/_fabknowledge_

* Semiconductor Blog:

* Personal Blog:

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(01:05) - Doug’s Background

(03:08) - How to Build Sector Expertise from Scratch

(04:37) - Why Moore’s Law is Dead and It’s Effect on the Semi Industry

(08:03) - Heterogenous Compute is the Next Paradigm Shift No One Is Talking About

(09:34) - Why Chip Specialization is Increasing

(13:12) - Understanding the Whole Semiconductor Supply Chain with a Restaurant Analogy

(20:51) - Where are Company Moats in the Semi Supply Chain

(26:54) - What are the Different Types of Chips (ASICs, CPUs, GPUs, FPGAs) and Why Do They Exist

(32:08) - The “DevOpsification” of Chips (i.e. specialized micro services)

(36:09) - LLMs (AI) and Semis Role in Powering the Tech Forward

(40:49) - Potential Reasons (Bear Case) for why Chip Usage May Slow

(43:05) - Tying Specialized Software to Chips - Nvidia’s Vertical Strategy

(47:45) - Favorite Technology/App

(49:09) - Favorite Snack

Additional Show Notes:

* Heterogenous Compute: The Paradigm Shift No One is Talking About

* Tech Monopolies Go Vertical

* The Rising Tide of Semiconductor Cost

* Semiconductor Blog:

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

For those excited about Open Source, data, and understanding Facebook’s high performance culture, this is the episode for you!

Nick Schrock is the Founder of Dagster Labs and previously Co-Creator of GraphQL while at Facebook. In this episode, we discuss how Facebook maintained a culture of urgency and decentralization. Nick dives into the problem solved behind GraphQL’s creation and how the product rolled out within Facebook. We also cover the modern data stack and how Dagster Labs is moving beyond the orchestration layer to provide more value to data engineering workflows. Finally, we discuss Nick’s decision to transition from the CEO role and advice he has for other founders in the Open Source space.

Where to Find Nick:

·       Twitter: https://twitter.com/schrockn

·       LinkedIn: https://www.linkedin.com/in/schrockn/

Where to Find Shomik:

·       Twitter: https://twitter.com/shomikghosh21

·       LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

·       Newsletter: https://www.shomik.substack.com

·       Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(00:56) – Joining Facebook During “Move Fast & Break Things” Era in 2009

(06:06) – Why Facebook Open Source Has Proliferated So Well

(09:04) – How Facebook Culture Changed to “Move Fast With Stable Infrastructure”

(10:56) – Making the Shift From Mobile to Desktop

(12:33) – Creating GraphQL

(16:50) – Finding Space to Work on GraphQL (Power of Decentralized Decision Making)

(18:34) – Rolling out GraphQL to All Facebook Developers

(21:14) – Why Not Start a GraphQL Focused Company

(23:12) – Starting Dagster

(27:35) – Learnings from GraphQL Translated to Dagster

(30:24) – Do Things That Don’t Scale Moment at Dagster

(32:50) – Evolving Dagster Labs to a Platform from Single Product

(35:15) – How the Practice of Data Engineering Differs from Data Engineers

(37:12) – Transitioning from CEO to CTO

(40:48) – How Did the Shift Immediately Feel Like After

(42:18) – Advice for Open Source Founders

(45:07) – What’s Coming Next for Dagster Labs

Show Notes:

-       Nick’s Post on Learnings from CEO Transition

-       Dagster Labs Platform Launch Week

How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube

For those interested in understanding how to drive high performance teams, create focus in an organization, and drive organizational excellence, this episode is jam-packed with tactics and anecdotes across software industries.

Zack Urlocker is an active Board Member and advisor to many different startups. His resume is too long to fully write out but he previously has served as CEO, COO, VP Marketing, VP Product, and VP Engineering across 7 different companies including Duo Security, MySQL, Zendesk, Gatsby, Netlify, Active Software, and Borland Software. Almost all of these he has joined at an early stage and he has numerous experiences scaling companies from $6-100M+ ARR with over 4 $1B+ outcomes. We discuss lessons learned from each company, complete with anecdotes and compounded knowledge that helped Zack improve along his career. He shares detailed advice on building customer obsession, aligning organizations around one focus area, and maintaining speed as a key advantage for startups as they scale. We also discuss how to build operational rigor at high scale in a constrained capital environment. There are too many learnings in this episode to fully write out.

Where to Find Zack:

·       Twitter: https://twitter.com/ZUrlocker

·       LinkedIn: https://www.linkedin.com/in/zurlocker/

·       Substack: https://buildtoscale.substack.com

Where to Find Shomik:

·       Twitter: https://twitter.com/shomikghosh21

·       LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

·       Newsletter: https://www.shomik.substack.com

·       Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(01:17) – How Zack Has Successfully Scaled 4 Companies to $1B+ Exits

(02:30) – Finding Customer Patterns Early in a Company’s Journey

(04:04) – Roles Across Various Software Industries & Business Models

(06:02) – Borland Software Lessons (Developer Software) – Scaling During a Turbulent Time Pre Dot Com Bubble

(13:18) – Active Software Lessons (Integration Middleware) - Scaling from $6-100M+ ARR in the Dot Com era

(17:15) – MySQL Lessons (Database Software) - Fixing Engineering & Running Marketing While Scaling from $6-100M+ ARR

(28:26) – Utilizing Customer Patterns to Find Free Users Who Are Likely to Pay at MySQL

(34:02) – Tips for Building Effective Remote Teams

(38:16) – What Customer Orientation Really Looks Like

(40:44) – Zendesk Lessons (Customer Service Software) – Scaling from $6-100M+ ARR in SaaS rather than infra

(47:01) – SaaS Pricing Dynamics

(52:27) – Duo Security Lessons (Multi-Factor Auth) – Scaling from $6-100M+ ARR in Security (vs infra & SaaS)

(1:00:25) – Why Speed & Customer Empathy = Efficient Software Businesses

(1:03:25) – “Figure Out Most Important Initiative, Put Best People On It, Starve Other Initiatives”

(1:07:43) – You Can’t Hedge In Product Strategy, Make Core Bets & Commit

(1:13:50) – Gatsby (Fronted Tooling) – Stabilizing a Company for Enterprise with a Large OSS Userbase

(1:17:36) – How to Orient Around Meaningful Customer Use Cases & Build Product & Go-To-Market Around That

Show Notes:

* Build to Scale Substack

* Finding Customer Patterns

* Finding Product Market Fit

* Getting Product Positioning Right

How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube

This episode is a perfect fit for anyone who wants to learn how to apply AI into their product especially for high fidelity analytics use cases.

Utkarsh Ohm is Director of AI at Thoughtspot. He previously was a Co-Founder & eng leader at various startups. In this episode, we cover applying LLMs alongside other models to customer facing products. We discuss where LLMs in particular are helpful vs traditional ML models, why text to SQL use cases need to be supplemented by internal insights to improve accuracy, and how to approach data security for LLMs. We deep dive specifically into Sage, Thoughtspot’s LLM enabled product and the infrastructure that allows Sage to produce accurate insights for customers. Over the course of the episode, we discuss plenty of advice for teams building with LLMs to learn from and take into account.

Where to Find Utkarsh:

* Twitter: https://twitter.com/utkarshohm

* LinkedIn: https://www.linkedin.com/in/utkarshohm/

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Newsletter: https://www.shomik.substack.com

* Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(01:35) - Utkarsh’s Journey to Becoming Director of AI at Thoughtspot

(03:14) - Learning AI/ML on the Job

(05:08) - Emergent Capabilities of LLMs Leading to Experimentation

(06:52) - AI Used in Thoughtspot Products in 2018

(10:30) - The ChatGPT Moment

(12:16) - How Sage (the LLM Powered Product) Works

(13:44) - 3 Key Capabilities of Building an Analytical Q&A System

(16:15) - Why Thoughtspot Doesn’t Use LLMs for Text to SQL

(20:35) - Why Models Currently Aren’t Good Enough for Analytical Understanding

(23:15) - The Infra Architecture Behind Sage

(29:55) - How to Approach Data Security for Applied AI Products

(33:15) - Customer Outcomes from Using Sage

(38:30) - Managing Hallucinations in the Hands of Customers

(42:40) - Advice for Teams Building LLM-enabled Products

Show Notes:

* Security and Risk Mitigation in an LLM World

* ThoughtSpot Sage Product

How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube.

This episode is a perfect fit for anyone who wants to get tactical insights on how to automate aspects of the SDR role without sacrificing quality and first principles thinking on managing inbound leads.

Hank Taylor is a Fractional CMO & advisor to many different startups. He previously was VP Marketing & RevOps at Vercel and held leadership & IC roles at companies like Gitlab, Neo4j, and Tray.io. In this episode, we get tactical from the start. Hank walks through specific email collateral and messaging workflows to mature developer leads after initial auth in. He walks through how SDR automation works and how to structure SDR teams around this tooling to make them more effective. He also covers why Product Advocates (technical SDRs) can be more impactful for companies selling technical products vs traditional SDRs. He explains the concept of Product Advocates, how to hire and train for that role, how compensation should look like, and future career paths for this role. Finally, we cover some of his most common startup advice on the marketing and inbound side.

Where to Find Hank:

* Twitter: https://twitter.com/theHankTaylor

* LinkedIn: https://www.linkedin.com/in/devmarketer/

* Website: https://www.growthsprint.dev/build-a-technical-sdr-team (discount code for workshops: “boldstart”)

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Newsletter: https://www.shomik.substack.com

* Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(02:10) - How Hank Automates the SDR Function

(09:15) - Building the Automation Utilizing Eng Help & Low Code Tooling

(12:28) - Detailed Walk Through of Email Sequences, Content, & Thought Process Behind SDR Workflow Automation

(22:48) - Why Innovate on the SDR Function with Product Advocates

(29:48) - What Are Product Advocates / Technical SDRs

(32:57) - Where to Find & How to Train Product Advocates

(38:02) - How to Compensate Product Advocates

(39:26) - Goals for Product Advocates

(43:00) - Common Advice for Startups

(45:57) - How Founders Can Manage Building This Automation & Function

(48:59) - 80/20 Rule for Pipeline Generation

(50:52) - Learnings from Founders of Vercel, Gitlab, & Others

Show Notes:

* Hank’s Workshop on How to Hire Product Advocates for Pipeline Generation - Use Following Promo Code for Discount: “boldstart”

* Blog Post Walking Through the Technical SDR Concept

* The Only Two Rules for Writing Any Email

"How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube.

At Atlassian’s scale, it’s mind-boggling to consider how rapid innovation and product architecture changes are implemented on a daily basis. This episode covers the “how” spanning effective team collaboration to cloud transitions.

Swati Raju is Head of Engineering, Confluence Cloud at Atlassian. She previously was a CTO, eng manager and IC at various companies including Groupon, Yahoo, and Ticketmaster. In this episode, we cover how Swati builds effective remote engineering teams. We also cover how Atlassian was able to shift from server to cloud while mitigating the impact on customers during this huge architecture shift. Finally, we dive into where Confluence is leveraging AI to improve the user experience and help customers be able to better accomplish their work. There’s learnings in this episode from early stage to massive scale.

Where to Find Swati:

* LinkedIn: https://www.linkedin.com/in/swati-raju-5557422/

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Newsletter: https://www.shomik.substack.com

* Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(01:25) - Building Effective Remote Eng Teams

(04:23) - Maintaining & Building Culture Remotely

(07:59) - Goal Setting to Enable Decentralized Decision Making

(10:28) - Balancing Resiliency & Innovation

(12:36) - Rituals & Anti-Patterns for Remote & Cross-Team Collaboration

(20:21) - Managing Transition from Server to Cloud

(25:23) - Building Enterprise Grade Products

(29:42) - Preparing for and Managing Downtime

(33:49) - AI’s Impact on Knowledge Workflows Across Atlassian Products

(37:04) - Starting with Thinner Slices of the Product to Iterate with AI

(40:41) - Main Challenges with AI Adoption Today

Show Notes:

* Confluence Whiteboards

How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube.

Nowadays we hear about “the consumerization of IT” and removing friction from user funnels everywhere. This episode covers how sometimes that can be the wrong move for the business even if users and the market think a freemium go to market is the best approach.

Bobby Pinero is Co-Founder & CEO of Equals, a next-gen spreadsheet. He was previously the first finance hire at Intercom and employee 20. In this episode, we cover why Freemium didn’t work for Equals and how Free Trial is actually a better fit. Bobby describes tips for building a horizontal product, how he approaches founder driven marketing, lessons from Intercom and how even seemingly small internal communication emails can have a massive impact on the business. This episode debunks a lot of popular blog posts out there now and instead focuses on first principles thinking to arrive at what makes sense for each business and product.

Where to Find Bobby:

* LinkedIn: https://www.linkedin.com/in/bobbypinero/

* Twitter: https://twitter.com/bobbypinero

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Newsletter: https://www.shomik.substack.com

* Podcast: Apple Podcasts, Spotify, YouTube.

In this episode, we cover:

(00:44) - What Equals Does

(03:38) - Building a Horizontal Product

(08:15) - Guiding Different Personas Through the Product

(10:55) - Leveraging Templates for User Adoption

(12:26) - Product Market Fit and Bespoke Onboarding

(14:06) - Deciding to Go Freemium

(15:36) - Why Retention Decreased as a Result of Freemium Without Top of Funnel Growth

(18:40) - How Some Friction Can Help Users Discover the Product

(20:06) - Reversing the Freemium Decision

(22:22) - Why Free Trial is Working Well

(24:07) - Equals Vs Intercom Go-To-Market Motions

(26:58) - Overcoming the Data Connectors Friction

(28:23) - Founder Driven Marketing

(30:28) - Showing the Product Through Consistent Product Demos & Launches

(32:49) - Learnings from Intercom

(34:34) - Jobs to Be Done for Intercom & Equals Aligning to Pricing & Packaging

(36:57) - Doing Things That Don’t Scale for Basic Reporting with a Big Impact

(40:05) - Setting a Culture of Showing the Product, Challenges, & Wins

Show Notes:

* Blog Post Describing Equals Decision to Stop Freemium

* Bobby’s Demo of Equals’s Newest Product - Dashboards

How to Subscribe:

Available on Apple Podcasts, Spotify, YouTube.