Shows
TrailblazersShomik Ghosh: Newest Partner at Sierra Ventures!Shomik is the newest partner at Sierra Ventures! A longtime venture investor and an inception-focused fund backing technical founders at day zero. He supported companies like Cloudquery, Kiln AI, and Ask-Y, and played a role in many other early investments.Shomik was an investor at Top Tier Capital, where he focused on growth-stage companies including CircleCI, Anaplan, Remitly, Shape Security, and Snyk. His path into venture was anything but traditional, with early experience spanning tech M&A, venture debt, a failed startup, and fixed income sales and trading.Originally from New Jersey and a Pittsburgh...
2026-01-271h 02
The Peel with Turner NovakInside the New Superhuman: $700M ARR, 40M Daily Users with Rahul VohraRahul Vohra is the Founder and CEO of Superhuman Mail.Rahul sold his company to Grammarly in July of 2025, which had just acquired Coda in 2024. Following the acquisitions, the combined companies rebranded to Superhuman in October of 2025.And it’s quietly one of the most underrated businesses that no one is talking about, with over $700 million ARR and 40 million Daily Active Users. Grammarly spent 15+ years building integrations with over a million other products, that they’re now layering more AI products on top of.We t...
2025-11-201h 39
On The FrontierBuilding AI Infra at Cloudflare - Dane Knecht (CTO, Cloudflare)Cloudflare has retained exceptional talent, continued shipping products at a rapid scale even as they’ve grown to a $80B+ valuation, and are positioned as a leading developer platform for the agentic era with Workers. One of the key individuals who has guided this effort has been Dane Knecht, CTO at Cloudflare and the first PM hired when < >In this episode we dive into the following areas:* Lava Lamps!* Cloudflare’s Culture from Day 1* Enterprise & Individual Developer Focus* Deep Dive into the Workers Platform* Building Agents on Workers
2025-10-3139 min
Yet Another Value PodcastShomik Ghosh's $CWAN bull thesisIn this episode of Yet Another Value Podcast, host Andrew Walker welcomes returning guest Shomik Ghosh for a deep dive into Clearwater Analytics (C-WAN). Known for his detailed research, Shomik breaks down C-WAN’s business model, recent acquisitions, valuation metrics, and long-term growth outlook. They explore how Clearwater’s sticky, cloud-native platform is disrupting legacy financial systems and what makes its data architecture and integration vision compelling. From insurance to asset management and hedge funds, the conversation unpacks how Clearwater aims to become an end-to-end solution across the investment lifecycle. They also discuss private equity involvement, AI applications, and valu...
2025-09-2253 min
On The FrontierIdentity in the Age of AI - Arnab Bose (Chief Product Officer, Okta Platform)A huge challenge coming to the exponential growth of AI agents is security and auth. Enterprises will have challenges adopting agents in critical workflows without these. There’s a race to solve this problem and today we’ll hear from one of the largest identity security companies leading the charge.Arnab Bose is the Chief Product Officer of Okta Platform and previously was VP Product at Salesforce and Quip. In this episode we dive into the following areas:* Okta’s Role in Identity & Security Across Entire Enterprises* AI’s Impact on Internal Workflows* H...
2025-06-0447 min
On The FrontierBuilding AI Products at Amazon & Amazon Q - Anoop Deoras (Director, AWS Agentic AI)Large tech companies have been rapidly embracing AI. Amazon in particular has been innovating rapidly with many recent announcements (Nova, Tranium 3, Bedrock Agents, & more), this episode dives into Amazon Q and Agentic AI at Amazon / AWS.Anoop Deoras is the Director of AWS Agentic AI and previously was a Principal Technologist at Netflix. In this episode we dive into the following areas:* The progression of AI over ~20 years* Building recommendation engines before Transformers* How AWS approached building Amazon Q* State of Coding Agents Today and Biggest Challenges around CodeGen
2025-05-1445 min
On The FrontierBuilding AI Driven Workflows - Eoin Hinchy (CEO, Tines)For those who are interested in how AI is impacting workflows of teams across industries, this is the episode for you.Eoin Hinchy is the CEO & Founder of Tines, a workflow builder for security-minded teams. He was previously the Sr Director of Security for Docusign and practiced security engineering at many others startups and corporations previously. In this episode we dive into the following areas:* The Founding Story Behind Tines* The Evolution of SOAR (Security Orchestration, Automation, & Remediation) over the past 10 years* How Tines Moved From Building for Security Teams to...
2025-03-1843 min
On The FrontierEnterprise News - March 11 w/ Ron Miller (Editorial Director, Boldstart)For anyone who’s interested in a recurring podcast that covers the Enterprise news from the past few weeks, this is the episode for you. In this episode, Ron Miller (Editorial Director, Boldstart) & Shomik Ghosh (Partner, Boldstart) dive into key Enterprise Software news from the 2 weeks prior. This is the first such episode and we’d love to hear your thoughts! Please let us know if you’d like to hear this more by reaching out, commenting, tweeting, etc!* Nvidia Earnings* OpenAI GPT 4.5 release* Microsoft leasing vs building datacenters (along with a canc...
2025-03-1151 min
Trends with FriendsFrom Meme Coins to Tariff Wars: Why AI, Crypto, and Markets Are Riding the Volatility RollercoasterJoin Howard Lindzon, Michael Parekh, Phil Pearlman, and special guests Adeniyi Abiodun (Co-Founder of Mysten Labs and Sui) and Shomik Ghosh (Investor at Boldstart Ventures) for a jam-packed episode of Trends with Friends. This week, the crew dives into the wild world of crypto, AI, and global markets. From peak degeneracy in stocks like Tesla, Palantir, and Solana to Sui's rise in Web3 and why cybersecurity is more critical than ever, this episode has it all. Plus, insights on Nvidia’s dominance, the next wave of Web3 consumer apps, and the geopolitical risks shaping the economy.📅 Recorded live on Febru...
2025-02-261h 11Yet Another Value PodcastBoldstart Ventures' Shomik Ghosh on Kelly Partners' $KPG.AX unique accounting firm roll-up strategyShomik Ghosh, Partner at Boldstart Ventures, joins the podcast for the second time to discuss his thesis on Kelly Partners (ASX: KPG / OTCQX: KPGHF), a specialist chartered accounting network established in 2006 to provide a better service to private clients, private businesses & their owners, and families.For more information about Shomik Ghosh and Boldstart Ventures, please visit:https://boldstart.vc/Chapters:[0:00] Introduction + Episode sponsor: Daloopa[2:20] Who is Kelly Partners and why they are so interesting to Shomik[5:31] What is Shomik seeing that the market is missing with Kelly Partners
2025-02-071h 07
On The FrontierData Streaming for AI - Andrew Sellers (Head of Technology Strategy, Confluent)This episode is for whomever is interested in data workloads for AI particularly event streaming and how those will be used in AI model training and inference.Andrew Sellers is the Head of Technology Strategy at Confluent. He was previously CTO at QOMPLX and CTO of the US Air Force Academy. In this episode, we dive into technology in the government and what changes for event streaming in the context of AI models. We cover technical aspects of data streaming, customer use cases for AI & event streams, and differences between inference workloads and training workloads for data...
2025-02-0542 min
On The FrontierAI Security in Coding Workflows - Ty Sbano (CISO, Vercel) & Emilio Escobar (CISO, Datadog)This episode is for whomever is curious about diving deep into AI Security and how CISOs think about it within internal and external workflows. Ty Sbano is the CISO of Vercel, the leading web experience hosting and deployment platform. He was previously CISO at Sisense and previously Sr Director of Security at Lending Club, Target, and Capital One. I’m also joined by Emilio Escobar, CISO of Datadog as a co-host. In this episode, we dive into how AI changes security practices, how to manage AI security around external products and internal workflows, and whether AI leverages ex...
2024-12-1946 min
On The FrontierDriving Growth in Design & AI - Caroline Mack (COO, Spline AI)This episode is a fit for anyone who’s interested in how to drive best of breed growth at companies like Spline AI, Canva, and many others.Caroline Mack is COO of Spline. Caroline previously was a Growth lead at Canva and worked in product & growth at companies like Tencent, DocuSign, Google, and TripAdvisor. In this episode, we cover tactical learnings about growth in the application layer and how AI is changing 3D design and driving value to users. We also cover product, growth, and pricing advice for all startups.Where to Find Caroline:...
2024-12-0538 min
On The FrontierThe Future of AI Agents - Joao Moura (CEO, CrewAI)For anyone who’s been curious about what AI Agents are, what they will do, and current deployed use cases at large enterprises, this is the podcast for you.Joao Moura is Founder & CEO of CrewAI, the leading multi-agent platform. He previously was Director of AI Engineering at Clearbit which was acquired by Hubspot. I’m also joined by my colleague Eliot Durbin at boldstart ventures. We are fortunate to partner with Joao as a founder in our portfolio! This episode dives deep into the multi-agent world talking about how agents work, the tech behind the scenes, unlo...
2024-10-2259 min
On The FrontierTactical Lessons from Founding 3 Companies - Ryan Denehy (CEO, Electric AI)For any founders or managers navigating go-to-market, strategy and org structure, this is the episode for you.Ryan Denehy is Founder & CEO of Electric AI, a leading SMB IT management platform. He previously founded two companies: Royalty Media (sold to USA Today) and Swarm (sold to Groupon). Ryan is never afraid to share detailed advice from his own journey and also from advising/investing in other founders. This episode is rich with insights on how to identify and execute pivots, matching product and go-to-market, and why company building relies on manual hard work at every stage. Ryan...
2024-07-2448 min
On The FrontierFrontier AI Research & Agents in the IDE - Madhav Singhal (AI Engineer, Replit)This episode is for builders experimenting in AI. We dive deep into technical aspects of agent based workflows, data models, and interesting new fundamental research.Madhav Singhal is a lead AI researcher at Replit focused on the frontier of what AI can enable for Replit users. In this episode, we dive into specific applications of models across code generation, testing, programming languages and more. We get fairly technical into how data maps to ML models and the types of agent based workflows that work today or may work in the future. We cover why focusing time on...
2024-06-2451 min
On The FrontierScaling MongoDB from Employee #8 - Meghan Gill (SVP Sales Ops, MongoDB)This episode is perfect for those interested in tactical advice from seed stage to IPO around marketing tactics and sales compensation.Meghan Gill is SVP Sales Operations & Sales Development at MongoDB. She previously joined as employee #8 and has scaled with the org over the past 15 years. In this episode, we cover tactical learnings about early and scaled marketing & sales compensation approaches. We tackle how to incentivize sales teams and how educational content can be effective lead gen for an early go-to-market motion. Meghan also shares many anecdotes from the scaling journey at MongoDB with advice for founders...
2024-06-0445 min
On The FrontierA Canva Deep Dive - Sandy Kory (Partner, HorizonVC)For those curious about the $25B valued business of Canva, this episode is the deep dive you’ve been waiting for.Sandy Kory is the Founding Partner of HorizonVC, an early stage VC fund, and an angel investor in Canva. In this episode, we cover everything about the company. How it scaled to $2B ARR growing 50-60% while being cash flow positive, it’s unique product and go-to-market motion, and how AI will continue to drive the next leg of future growth. Sit back and enjoy this masterclass on Canva.Where to Find Sandy:...
2024-05-2154 min
On The FrontierHow Enterprise Software Powers Capital Markets - Sid Bala (CIO, Data & Analytics, BNY Mellon)For those interested in learning about how tech powers capital markets and how enterprises approach digital transformation, this is the episode for you.Sid Bala is the CIO of Data & Analytics at BNY Mellon. He is also Head of Public Cloud at the bank. In this episode, we chat about how to approach enterprise scale transformations & architecture and taking a portfolio approach to using new and existing tech. We also cover the use cases for Generative AI and how data sharing advancements across enterprises will continue to change the landscape in the future. This is a great...
2024-05-1444 min
On The FrontierA OneTrust Deep Dive - Kumar Gautam (Partner, Sands Capital)For those interested in learning about OneTrust (last valued at $4.5B), this is the episode for you.Kumar Gautam is a Partner at Sands Capital, a multi-strategy asset manager where he focuses on the late stage venture practice. In this episode, we do a deep dive into OneTrust, the ~$500M ARR business that is scaling rapidly in the data privacy, trust & GRC space. We cover all the aspects of the business in depth including the platform, customer use cases & personas, competitive landscape, go-to-market motion, and the future ahead.Where to Find Kumar:* Twitter...
2024-05-0242 min
Venture with GraceShomik Ghosh: Navigating Enterprise Software VenturesShomik is a Partner at boldstart and has over 6 years of venture investing in enterprise software. He’s experienced all the highs and lows of the entrepreneurial journey from IPOs and acquisitions to a failed startup. And is uniquely positioned to help pre-product enterprise startups.
Prior to boldstart, Shomik worked as a growth stage investor at Top Tier Capital where he invested in companies like CircleCI, Anaplan, Area 1 Security, and Shape Security. His experience ranges from investment banking, to startups, and finally venture capital. He first interacted with startups doing venture debt and then joined a startup as the fi...
2024-04-241h 02
On The FrontierEnterprise Tech Behind Digital Banking - James Barney (Director Cloud Platform Eng, Ally Financial)This episode is a great balance of the high level impact of AI & Cloud on enterprise use cases and detailed tech deep dives behind how they’re powered. Whether you’re a CIO, Founder, or IC, there’s stuff in here for everyone.James Barney is Director of Cloud Platform Engineering at Ally Financial. He previously was a data engineer at Accenture and Lowe’s. In this episode, we cover how Ally as a digital bank builds and utilizes cloud technology to deliver a great experience to customers. We talk about migrating through modern tech transitions, centralizing data for...
2024-04-2344 min
On The FrontierNvidia, Groq, HBM & What's Ahead for Semis (Doug O'Laughlin, Founder of Fabricated Knowledge)The most important trend powering AI is semiconductors and that trend is not slowing down anytime soon. We need to understand what is happening at the semiconductor level to be able to project forward what we think will occur in AI. This episode is the best way to learn what’s ahead of semis.Doug O’Laughlin is the first 2nd time guest on Software Snack Bites! He is the Founder of Fabricated Knowledge which is one of the fastest growing and highest grossing newsletters out there. The reason for that is because each of his write-ups is p...
2024-04-091h 03
On The FrontierA Peek Behind the Hacker Curtain - Douglas Day (Top Grossing Hacker, HackerOne & Sr Security Eng, Elastic)We hear about hackers all the time but very rarely get a glimpse into the world of what they actually do when exploiting applications. Douglas Day is a top grossing hacker on the HackerOne platform and a Senior Security Engineer at Elastic. In this episode, we dive into all things bug bounties and ethical hacking. How does Douglas find entry points, differences between defensive and offensive security, and escalating user permissions to find deep vulnerabilities are all covered. We also talk about common attack patterns for Douglas and other hackers and why WAFs are more annoying then useful.
2024-04-0252 min
On The FrontierScaling Product & Operational Excellence - Charles Zedlewski (COO, Temporal & GM, Cloudera)Scaling companies is incredibly difficult but at each stage the building blocks need to be set in place properly. Charles Zedlewski has been COO, GM, and a product leader at companies like Temporal, Cloudera, and SAP. In this episode, we cover what the COO & GM roles do, stories from early Cloudera days especially around figuring out what products to sell and pricing and packaging. We cover hiring Player/Coaches, nailing positioning, and talk about countless anecdotes from both Temporal and Cloudera to learn how to build and scale a great org.Where to Find Charles:· Twitter...
2024-03-271h 04
On The FrontierAI Agent-Assisted Flow Engineering - Itamar Friedman (CEO, CodiumAI)For those interested in the future of autonomous software testing & code generation, this is the episode for you.Itamar Friedman is Co-Founder & CEO of Codium AI. He previously was Head of AI at Alibaba Israel and a founder of multiple startups before that. In this episode, we cover why Prompt Engineering is shifting into Flow Engineering. We dive deep into the areas of software verification and testing. We talk about how to bring up a world of zero bugs in software development and what agent-assisted code generation, testing, & completion looks like. We also cover how future coding...
2024-03-2046 min
On The FrontierState of Developer Tooling - Redmonk (James Governor & Kate Holterhoff)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 d...
2024-03-1248 min
On The FrontierTime Management for Knowledge Workers - Matt Martin (CEO, Clockwise)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.co...
2024-03-0545 min
On The FrontierHealth 101 for Entrepreneurs - Ben Canning (Founder, We Hack Health)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...
2024-02-2758 min
On The FrontierReplay: Doug O'Laughlin (Founder, Fabricated Knowledge) - A Detailed Primer on the Semiconductor IndustryGiven 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 take...
2024-02-1352 min
On The FrontierNick Schrock (Founder, Dagster Labs & Co-Creator, GraphQL) - Facebook Eng Culture & Modern Data Stack ConsolidationFor 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 deci...
2024-02-0647 min
On The FrontierZack Urlocker (Exec - Duo Security, MySQL, Zendesk, Gatsby/Netlify) - Driving Operational Excellence Across Four $1B+ Outcomes From $6-100M ARR+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...
2024-01-241h 22
On The FrontierUtkarsh Ohm (Director of AI, Thoughtspot) - The Future of AI Powered Search & AnalyticsThis 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...
2024-01-1546 min
On The FrontierHank Taylor (Fractional CMO & Former VP Marketing, Vercel) - How to Automate the SDR Function & Hiring Product AdvocatesThis 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...
2024-01-0954 min
On The FrontierSwati Raju (Head of Eng, Confluence Cloud, Atlassian) - AI's Impact on Workflows, On Prem to Cloud Transitions, Building Effective Remote Eng TeamsAt 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...
2024-01-0345 min
Total Rekall - A podcast for anyone and everyone in the tech startup communitye012 - Shomik Ghosh: The Startup Landscape in 2023 and beyond
In this episode of the Total Rekall podcast, host Will Bourne from Rekall Consulting dives into the world of startups and venture capital with Shomik Ghosh from Bold Start Ventures.
The conversation revolves around the unique challenges and opportunities faced by startups in the post-COVID era. Shomik shares valuable insights into the journey of Bold Start Ventures through 2023, emphasizing the importance of backing technical founders in enterprise software from the earliest stages. The discussion covers various topics, including hiring strategies, the impact of recent global events on startups, and the vital role of resilience...
2023-12-2034 min
On The FrontierBobby Pinero (CEO, Equals) - Why Freemium Doesn't Always WorkNowadays 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 approa...
2023-12-1942 min
On The FrontierFergal Reid (VP AI, Intercom) - Applied AI Insights from Shipping Fin (an LLM enabled chatbot)Intercom was shipping and experimenting with AI enabled products since 2017. This episode is for those interested in hearing about the evolution of AI models, the customer results, and how these models can be applied in production.Fergal Reid is Vice President of AI at Intercom. He started at Intercom nearly 7 years ago to help the company begin delivering products leveraging AI. In this episode, we cover how ML & AI has evolved since 2009 and why the reasoning engines that exist in models today are a substantial improvement. We dive into Intercom’s AI-enabled products starting in 2017 to now Fi...
2023-12-1239 min
On The FrontierChris Huskey (Partner, Octahedron Capital) - A Databricks Deep DiveOne of the most exciting private companies today is Databricks, growing over 50% at $1.5B ARR with a recent valuation of $43B announced in September 2023. This is the deep dive you’ve been waiting for to understand the product, growth, and competitive landscape.Chris Huskey is a Partner at Octahedron Capital, a hedge fund that invests in public and private markets. Databricks is a large position in Octahedron’s portfolio. In this episode, we cover every aspect of Databricks. The origin story, culture & ethos of the company, TAM expansion, platform components, competitive dynamics, financial metrics, and the future ahea...
2023-12-051h 01
On The Frontier#26 - Marten Mickos (CEO, HackerOne & prev CEO, MySQL & Eucalyptus Software) - The OG of Open Source, Lessons Learned Scaling Multiple Enterprise Software Startups, Tactical Leadership LearningsCurious about how to scale Open Source companies. Want to hear anecdotes of existential company killing moments that turned into defining assets? This episode has everything from leadership tactics, hard earned advice, managing in competitive industries, new category creation and much more.Marten Mickos is CEO of HackerOne and the OG of Open Source. He has 36+ years of enterprise software experience. His resume would take too long to fully cover but he previously was the CEO of MySQL (one of the first open source companies) and CEO of Eucalyptus Software. He’s also served as a board me...
2023-11-281h 18
On The Frontier#25 - Kunal Agarwal (CEO, Dope Security) & Emilio Escobar (CISO, Datadog) - Deep Dive into SSE & SASE Security, The Convergence of Networking & SecurityThis episode is for whomever is curious about Secure Service Edge (SSE) or Secure Access Service Edge (SASE) Security and why seemingly every public security company seems to be trumpeting their solutions in this space which Gartner predicts will be one of the fastest-growing categories of spend in the coming years.Kunal Agarwal is the Founder & CEO of Dope Security which is building a modern Secure Service Edge (SSE) platform. He was previously Sr Director of Product at Forcepoint and GM at Symantec. Kunal started his journey into security as a teenage hacker. I’m also joined by...
2023-11-1340 min
On The Frontier#24 - Glen Kacher (Chief Investment Officer, Light Street Capital) - AI's Potential Impact on Public Software Companies, How to Conduct Rigorous Research, Lessons learned from Julian RobertsonMany of us in the private markets are curious about how public markets view AI’s impact and the approach that public market investors take to investing in companies. This episode uncovers that from one of the top public software investors in my opinion.Glen Kacher is Chief Investment Officer at Light Street Capital. He founded Light Street 13 years ago after stints at Integral Capital Partners and Tiger Global. In this episode, we cover a long term successful public market investor’s view on how AI will impact the software industry and other industries as well. We talk...
2023-11-0735 min
On The Frontier#23 - Ethan Schechter (VP Sales & 1st Sales Leader, Snyk) - "Trade Dollars for Speed", "The Minute You Stop They Win", and More Tactical Advice for Sales from Early Stage to ScaleThis episode is packed with tactical advice for all things sales and go-to-market. It’s relevant across stages whether your company is at $0M ARR or at $100M+ ARR. Ethan Schechter is VP Sales at Snyk. He started at Snyk 6 years ago as the first sales leader. In this episode, we cover tactical insights from Ethan’s experience leading early sales to scale at Snyk and ZeroTurnaround. He describes how to position a product when “shift left” was a new and scary term, how to make first sales, tradeoffs to consider with early vs late stage deals. He share...
2023-11-0153 min
On The Frontier#22 - Kevin Wang (Chief Product Officer, Braze) - Scaling from Employee 5 to Public Company Exec, 0 to 1 Anecdotes and Advice for Early Stage Startups, Product Advice from early to scaleThis episode is useful for all founders, startup employees, and investors who are interested in early stage startup advice, enterprise product tips, and learning how employees can scale from Day 0 to public markets.Kevin Wang is Chief Product Officer at Braze. He started at Braze ~12 years ago as employee #5 going from software engineer, to PM, and eventually to CPO. In this episode, we cover learnings from Kevin’s incredible journey and how he as well as the company scaled from Day 0 to a public company. He shares stories, anecdotes and advice for other startups about the earliest da...
2023-10-1850 min
On The Frontier#21 - David Dorman (VP Self Serve, Grafana) - Open Source GTM, Developer First Marketing, Product Marketing & Self Serve TacticsThis episode is useful for all founders, startup employees, and investors who are interested in product marketing, self serve, and PLG for developer focused, enterprise software products.David Dorman is VP, Self Serve at Grafana and formerly Director of Product Marketing at DigitalOcean. In this episode, we cover learnings from DigitalOcean’s incredible content strategy, what Self Serve means and specific advice that David has for teams in this area, how developer marketing differs from Self Serve workflows, and advice for teams trying to improve their strategies in these areas. This is a tactical episode where David sh...
2023-09-2748 min
On The Frontier#20 - Alex Mackenzie (Tapestry VC) & Ian Livingstone (Snyk) - Round Table Explaining New Technologies - Javascript Runtimes, Edge Compute, Observability, Encryption, LLMs & AIThis podcast episode is a new format where I introduce everyone to my go-to brain trust to chat new technologies with. This episode can be consumed end to end or you can jump to specific categories that particularly interest you (timestamped below).Alex Mackenzie is a Partner at Tapestry VC and Ian Livingstone is a Team Lead at Snyk. In this day and age, there’s a new technology that seems to capture the interest of the ecosystem (particular tech Twitter) every month. When I need to dive into these technologies or have them explained, I go to...
2023-09-131h 03
On The Frontier#19 - Muji (Founder of Hhhypergrowth) - Data Infrastructure Trends, Operational vs Analytical Databases, Benefits of Edge Network Architectures, Emergence of SASE Security, Zero Trust SecurityThis podcast episode is for all of those who are interested in trends like cloud data warehouses, data & AI, edge networks, SASE security, zero trust security and companies like Snowflake, Databricks, Cloudflare, Z-Scaler, Palo Alto Networks, and of course the big cloud providers. Muji is the Founder of Hhhypergrowth, which is my favorite research publication for all things software infrastructure and security. I HIGHLY RECOMMEND subscribing. Can’t say enough about how worth it Muji’s research service is even for folks who are deep in infra and security as I am. I first came across Muji when...
2023-08-301h 02
On The Frontier#18 - Jake Saper (General Partner, Emergence Capital) - Moats in SaaS, AI's Impact on SaaS, Learnings from Salesforce, Zoom, Gusto & moreJake Saper is a General Partner at Emergence Capital which has backed leading SaaS companies like Salesforce, Zoom, Gusto, Bill.com, and Veeva. Jake is a Board member of companies like Guru, Textio, Ironclad, Maze & many others. When I wanted to do a deep dive into SaaS business models, I could think of no one better than Jake and this episode absolutely delivered. We cover everything from single-player to multi-player product modes, various moats in SaaS, and how SaaS pricing & business models are evolving. We dive into specific anecdotes from companies like Zoom, Guru, Textio and others around how...
2023-08-231h 05
On The Frontier#17 - Ian Swanson (CEO of Protect AI) & Emilio Escobar (CISO of Datadog) - Deep Dive into ML & AI Security, Emerging Attack Surfaces, MLSecOps, and LLMs Use in Adversarial and Defensive SecurityIan Swanson is the Co-Founder & CEO of Protect AI which secures AI and ML systems. He was previously the Co-Founder & CEO of Datascience.com which sold to Oracle, where he was VP AI & ML and then was Worldwide Leader of AI & ML at AWS before starting Protect AI. I’m also joined by Emilio Escobar, CISO of Datadog as a special co-host! In this episode, we dive into what is ML & AI Security, the different types of attacks that hackers are using, and how teams can best secure their systems. We also talk about MLSecOps and why an ML BO...
2023-08-1659 min
On The Frontier#16 - Jade Rubick (ex VPE at New Relic, Eng Advisor to Jeli, Flatfile, Mode, Maze & more) - Tactical Advice for Building Effective Eng Teams, Anti-Patterns for Eng Teams to AvoidJade Rubick is a Eng Advisor to multiple startups (23 and counting). He was previously Vice President Engineering at New Relic and has taken on interim VPE roles at multiple other startups over the years before he began solely focused on advising startups. In this episode, Jade joins us to cover common anti-patterns he sees in eng teams, how teams can better communicate, what hiring practices work well and how to think about structuring career paths for employees. Everything from hiring tips, to product & feature development, to adjusting to the current “do more with less” environment and common advice across all...
2023-08-0844 min
On The Frontier#15 - Julia Schottenstein (Product Lead @ dbt) - Trends in Analytics Engineering, Data Transformation & Semantic Layer Deep Dive, Open Source to Cloud Product LearningsJulia Schottenstein is a Product Lead at dbt and an active angel investor. Julia was previously a VC at NEA focused on software and data infrastructure. She joins us today to share learnings from product and VC, why analytics engineering is continuing to proliferate, and how dbt has been able to manage and grow the community over time. We dive into the data transformation and semantic layer and cover how dbt thinks about the open source and cloud products, managing feedback from all users to improve the product. We end with exciting trends for the future of data (hint...
2023-07-1947 min
On The Frontier#14 - Kiersten Gaffney (CMO of Codefresh, Advisor to AtomicJar, CodeSee, Fermyon, Redis & more) - Detailed Market Tactics for Dev Tools Founders, How Early Stage Companies Should Approach MarketingKiersten Gaffney is the Chief Marketing Officer of Codefresh and a Go-To-Market Advisor for AtomicJar, CodeSee, Fermyon, Redis & many more companies. Kiersten was previously a marketing leader at Buoyant and Mesosphere, with many years of experience in software infrastructure and developer tools. She joins us today to share detailed tactics for dev tools founders on how to “do more with less”, designing content strategies, and leveraging communities to propel go-to-market forward. We dive into hiring insights on what marketing personas to hire at what stage and talk about specific tactics that Kiersten employed at previous and current roles to gene...
2023-07-1138 min
On The Frontier#13 - Dan Scheinman (Board Member of Zoom, SentinelOne, Arista Networks) - Finding Outlier Founders & Angel Investing from Day One, Demystifying Public Boards, Winning in Competitive MarketsDan Scheinman is a full-time Angel Investor and Board Member of Zoom, SentinelOne, and Arista Networks. He joins us today to share learnings about M&A from his time running Corp Dev at Cisco, backing multiple public companies from day one, and how public boards differ from private ones. There’s numerous anecdotes that Dan shares about how he finds outlier founders, how founders are able to succeed even when they’re building in already competitive markets, and tons of actionable advice for founders today on everything from focus to capital allocation to M&A decisions. Where to F...
2023-06-2158 min
On The Frontier#12 - Phillip Carter (Principal PM @ Honeycomb) - All The Hard Stuff when Building Products with LLMs, Actual Results from Leveraging AIPhillip Carter is a Principal Product Manager at Honeycomb, which develops a software debugging product for distributed systems. Phillip recently published one of the most interesting blog posts I’ve read titled “All the Hard Stuff Nobody Talks About when Building Products with LLMs”. The post is excellent and everyone should give it a read. In this episode, we dive deep into what the hard stuff actually is, the pros and cons of Large Language Models (LLMs) and what teams need to think about when using LLMs in their products. We also talk about the real world results that come f...
2023-06-1450 min
BUILDERSFunding the Future: Shomik Ghosh, Partner at Boldstart VenturesIn today's episode of Category Visionaries, we speak with Shomik Gosh, Partner at Boldstart Ventures, a venture capital firm specializing in backing founders from before they’ve even laid down their first line of code, about why being part of a startup journey from the very first step is such a rewarding experience. Providing insights and support for everything from concept creation to preparing a market-ready offering, Boldstart believes in giving every founder with a truly game-changing idea the best possible chance of making their difference.
We also spoke about the venture space’s focus shifting back to p...
2023-06-0926 minBUILDERSFunding the Future: Shomik Ghosh, Partner at Boldstart VenturesIn today's episode of Category Visionaries, we speak with Shomik Gosh, Partner at Boldstart Ventures, a venture capital firm specializing in backing founders from before they’ve even laid down their first line of code, about why being part of a startup journey from the very first step is such a rewarding experience. Providing insights and support for everything from concept creation to preparing a market-ready offering, Boldstart believes in giving every founder with a truly game-changing idea the best possible chance of making their difference.
We also spoke about the venture space’s focus shifting back to p...
2023-06-0926 min
On The Frontier#11 - Julian Alvarez (CEO of Logixboard) - Building and Scaling a Vertical SaaS Company, Explaining Freight Forwarding & the Supply Chain IndustryJulian Alvarez is the CEO & Co-Founder of Logixboard, which is enabling freight forwarders to deliver a modern, digital customer experience to their customers with the Logixboard platform. He joins us today to talk about how to understand customer pain points in a specific vertical and gives a detailed overview of the freight forwarding and supply chain industry. Julian covers how to build a vertical SaaS software company, how scaling in vertical SaaS is different from other industries, and what sort of integrations and technology aspects vertical SaaS software companies need to take into account. For any founders, investors, or...
2023-06-0748 min
On The Frontier#10 - Mia Wang (M&A Director at Cloudflare) & Oren Falkowitz (Co-Founder of Area 1 Security) - Demystifying the M&A Process, Tips for Founders on Executing a Smooth ProcessMia Wang is the M&A & Strategy Director at Cloudflare. Oren Falkowitz is the Co-Founder of Area 1 Security, a phishing security company, which was acquired by Cloudflare in April 2022. In this episode, Mia & Oren demystify the M&A process for startups (founders and employees) by discussing the real steps and decisions that both sides had to make as the acquisition was being contemplated and completed. Tactical advice is shared all along the way for founders to learn from in order to enable the smoothest M&A process possible in the future.Where to Find Mia:...
2023-05-3157 min
On The Frontier#9 Kyle Poyar (Operating Partner at Openview) - Detailed Tips & Tactics for PLG motions, Pricing & Packaging, Product Led Sales & Marketing Tips, and Specific Case StudiesKyle Poyar is Operating Partner at Openview focused on PLG, pricing & growth. He writes the amazing and widely read newsletter, Growth Unhinged, which is one of my favorite weekly reads (multiple times a week!). It’s a wealth of information and I highly recommend listeners subscribe. Kyle joins us today to dive into all things PLG. He shares detailed and highly actionable tips with real-world examples of the countless startups he’s studied and worked with. We talk about PLG motions, multiplayer vs single-player, pricing & packaging, marketing tactics, retention and more. We could have gone on for much longer and...
2023-05-2458 min
On The Frontier#8 Seth Rosen (Head of Data Products at Snyk, Co-Founder of Topcoat Data) - A Modern Data Stack Overview, How Product Management & Data Teams Work Together, Future Trends in DataSeth Rosen is Head of Data Products at Snyk and previously Co-Founder of Topcoat Data, acquired by Snyk in March 2022. In this talk we cover, all things data, specifically diving into what the modern data stack is and the components that form it. We cover Seth’s experience working with customers of all sizes while he was running a data analytics consultancy, with tips for how companies can get value from data with a few core systems. Seth also explains what customer facing analytics enables and the path to achieving this. Finally, we dive into how LLMs may affect th...
2023-05-0940 min
On The Frontier#7 Brian Chambers (Chief Architect at Chick-Fil-A) - Technology Powering Fast Food, Enterprise Architecture, Edge Compute Use Cases, How New Technology is Adopted in EnterprisesBrian Chambers is the Chief Architect at Chick-Fil-A, which is one of the fastest growing fast food restaurants in the US. Brian has been with Chick-Fil-A for 19 years, where the company has gone from $1B to $19B in sales (a nice 19x in 19 years). He’s seen the software architecture evolve from through various technology shifts such as datacenter to cloud, mobile, edge compute, and much more. He joins us today to talk about Chick-Fil-As architecture, how the backend technology maps to real business use cases, and how Architects approach impacting the tech stack especially as waves of technology ar...
2023-05-031h 15
On The Frontier#6 Brian Douglas (Founder of OpenSauced, Dev Rel at Github & Netlify) - What is Developer Relations, How to Succeed at Dev Rel, Scaling Open Source Projects & ContributionBrian Douglas (aka Bdougie on all social platforms) is the Founder of OpenSauced, which is bringing enterprise insights and analytics to Open Source projects. He joins us today to dive into the open source ecosystem and the Developer Relations (DevRel) role. Brian was the 3rd engineer at Netlify and the 1st Developer Advocate at Github . In this episode, he talks about playbooks to create content that resonates with developers, how OSS projects can scale, and what is going on in the Jamstack ecosystem. Brian shares a ton of tangible examples from his own career of successful DevRel efforts that...
2023-04-1838 min
On The Frontier#5 Matt Butcher (CEO, Fermyon) & Steve Manuel (CEO, Dylibso) - Why WebAssembly is the Future of Computing, Current Use Cases for Wasm, What to Expect in the FutureSteve Manuel is the Co-Founder & CEO of Dylibso, which is creating developer tools to take WebAssembly to production. Matt Butcher is the Co-Founder & CEO of Fermyon which is building a cloud product to deploy & manage WebAssembly apps faster than existing cloud solutions. In this talk, both founders talk about why they are excited to build in the WebAssembly ecosystem, why Wasm is going to enable developers to have superpowers as the Wasm standards mature, and current companies & use cases that WebAssembly enables today. This episode strikes a great balance of giving a high level overview of why the technology...
2023-03-2959 min
On The Frontier#4 Doug O'Laughlin (@FoolAllTheTime) - Founder of Fabricated Knowledge, A Detailed Primer on the Semiconductor Industry, What Powers AI Under the Hood, Trends in Chips for the FutureDoug 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, th...
2023-03-2152 min
On The FrontierJamin Ball - Partner at Altimeter Capital, Cloud Metrics, Macro Viewpoint for Founders, Backing Essential Companies, Trends in Cloud Data InfraJamin Ball is a Partner at Altimeter Capital and previously at Redpoint Ventures. He joins us today to share learnings about cloud metrics and seat based vs consumption based pricing. Jamin shares specific thoughts on cloud data infrastructure, why cloud optimization goes in cycles, and how Altimeter invests through business cycles in essential long-term businesses. We also cover the macro environment that founders should be aware of, trends in inflation, and how it affects businesses.Where to Find Jamin:* LinkedIn: https://www.linkedin.com/in/jamin-ball-49366137/* Twitter: https://twitter.com/jaminball...
2023-03-0149 min
Scaling DevToolsShomik Ghosh - office hours with a DevTools investorShomik is a Partner at boldstart where he focuses on investing in Developer Tools and other enterprise software startups. What we coverAn introduction to ShomikWhere to start?Early stage versus late stageWhat should be Open Source?How to approach pricingWhat to do when things slow downWhere to hear from ShomikTwitter: @shomikghosh21Linkedin: https://www.linkedin.com/in/shomik-ghosh-a5a71319/https://shomik.substack.com/https://boldstart.vc/Interview with CISO of DataDog https://shomik.substack.com/p/emilio-escobar-ciso-of-datadog-how#details
2023-02-2338 min
On The FrontierEmilio Escobar - CISO of Datadog, How security companies can stand out from the noise, trust & safety vs security orgs, how enterprises manage securityEmilio Escobar is the CISO of Datadog and before that previously VP Security at Hulu and Application Security lead at Sony Playstation. He joins us today to share learnings from running security at various companies, tips for security founders to distinguish themselves from the rest of the noise, and how internal security works at enterprises. Emilio shares specific tips on how he structures security orgs and makes it so that security can be an enabler to the business. We also cover why security teams should be called Trust & Safety teams instead and the pitfalls that exist within the current...
2023-02-1551 min
On The FrontierDamian Schenkelman - Principal Architect at Okta, Scaling from Employee 10 to Exit at Auth0Welcome to Software Snack Bites the Podcast! This podcast will be an exploration of all things enterprise software from technology trend deep dives, to company building, to enterprise purchase decisions. Damian Schenkelman was Employee 10 at Auth0 and has played multiple roles in the company from early engineer, to first Director of Engineering, to Principal Architect at Okta/Auth0 Lab which is exploring new products in the auth space. He is also an angel investor and advisor to numerous startups and is happy to help any founders who reach out! He joins us today to share the journey...
2023-02-0851 min
On The FrontierSSB TeaserWelcome to Software Snack Bites the Podcast! This podcast will be an exploration of all things enterprise software from technology trend deep dives, to company building, to enterprise purchase decisions. This episode is a short quick Teaser describing what future episodes will cover!* Software Snack Bites Newsletter: https://www.shomik.substack.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit shomik.substack.com
2023-02-0701 min
The Business BrewShomik Ghosh - A SaaSy ConversationThe Business Brew is joined by Shomik Ghosh. Mr. Ghosh is a Principal at Boldstart Ventures, a day one, pre-product partner for technical founders with portfolio companies such as Snyk, Kustomer, BigID, Superhuman, Front, and Security Scorecard. His career has spanned everything from fixed income sales & trading to investment banking to venture capital. He specializes in enterprise software for his day job and long-term competitively advantaged businesses in his PA (a lot of which are also enterprise software companies 😀). Shomik has been trying to make Bill less stupid for almost two years now. He succeeded in...
2021-01-291h 55
Value Hive PodcastAll Things Enterprise Software w/ Shomik Ghosh, Boldstart VC (Ep. 57)This episode is brought to you by TIKR. Join the free beta today at TIKR.com/hive. They're constantly releasing new updates that make the platform better including a new Business Owner Mode that hides share count, market cap, and enterprise value. I couldn't be more excited to partner with TIKR.
Shomik Ghosh is a principal at Boldstart VC by day and resident Enterprise Software savant by night. Shomik's job at Boldstart VC is to find and become Day One partners with passionate, technical Enterprise Founders. This means Shomik spends all his time thinking, analyzing, and valuing...
2020-12-251h 20Yet Another Value PodcastMinion Capital (aka Shomik Ghosh) on Shopify and VC investingShomick Ghosh (aka Minion Capital), a Principal at Boldstart, talks about his experience as a Venture Capitalist and how he balances investing in both public and private companies. Then we dive deep into the investment case for Shopify (SHOP).Minion Capital twitter: https://twitter.com/MinionCapitalShomick's twitter: https://twitter.com/shomikghosh21Boldstart: https://www.boldstart.vc/
2020-10-031h 01