
Startup Field Guide by Unusual Ventures: The Product Market Fit Podcast
Every overnight success in the world of software happens after years of hard work finding product-market fit. The Unusual Ventures Startup Field Guide is a podcast for early-stage software leaders and aspiring founders looking for help going from 0 to 1. Featuring great conversations with successful startup founders, you will learn about hiring, product research, go-to-market, fundraising, and more.
Latest episodes

Oct 30, 2023 • 45min
Solo’s product-market fit journey: Idit Levine on timing the market for open source success
Solo is an open-source developer platform designed to connect applications with service meshes across any software infrastructure. Their core promise to their customer is to help them migrate from 10/20 year old legacy monolithic applications to new cloud native architectures with APIs and microservices.
Last valued at $1Bn, Solo has hundreds of enterprise customers including enterprises like TMobile, American Express, SAP, Sumo Logic, and more.
In this episode, Sandhya Hegde chats with Idit Levine, the founder and CEO of Solo.
Join us as we discuss:
1:13 Solo’s origin story
6:04 Early fundraising challenges
13:45 The technical insight that led to Solo
15:00 Studying the market to refine Solo’s product vision
16:49 API Gateway as a stepping stone for service mesh
21:58 Early customer acquisition efforts
24:33 Idit’s conviction in the API Gateway approach
25:26 How Solo found its first paying customers
29:25 Idit’s approach to founder selling
31:17 Idit’s evolution as CEO
36:50 Solo’s approach to open source community-building
40:50 Advice for founders building open source projects
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and
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Idit Levine is the founder and CEO of Solo.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.
Further reading from Unusual Ventures:
Starting an open source company
Hiring for an open source company
Building open source GTM

13 snips
Oct 16, 2023 • 31min
Writer’s product-market fit journey: May Habib on taking on ChatGPT Enterprise
Discover the journey of Writer, an enterprise-grade generative AI platform, from its origin story to addressing security and compliance in AI models. Hear about the importance of enterprise AI and the next horizon for Gen AI. Join CEO May Habib as she shares her insights on building a culture of curiosity at Writer.

Sep 25, 2023 • 47min
How open source AI will find product market fit: A conversation with Databricks, and AI startup Together
Founders of Databricks and Together discuss the rise of open source AI, building with open source, standardization of LLMs, the role of academia in AI research, innovations in training data, growing accessibility of machine learning with LLMs, the future of the open source ecosystem, and best practices for parameterizing LLMs.

Sep 11, 2023 • 47min
Deliverr's product-market fit journey: Michael Krakaris on enabling Prime for all E-commerce
Started in 2017, Deliverr is an E-commerce fulfillment company that integrates with marketplaces such as Shopify and Walmart. The company offers a two-day shipping service to small merchants selling on these online marketplaces helping them compete with Amazon Prime. Co-founded by Harish Abbott and Michael Krakaris, the company was acquired by Shopify for US$ 2.1 bn in May 2022.
In this episode, Sandhya Hegde joins Michael Krakaris and Sarah Leary (GP at Unusual) to discuss Deliverr’s path to product-market fit.
Join us as we discuss:
01:00 The insight that led to Deliverr’s founding
04:20 Why E-commerce fulfillment needed to be democratized
08:18 The value of understanding customers to achieve product-market fit
15:11 Early product-market fit signals for Deliverr
20:15 Pivoting Deliverr's business model to drive revenue
26:23 How Deliverr built and scaled its sales team
29:33 Deliverr’s breakthrough with Walmart
33:06 Deliverr's expansion: From Walmart partnership to multichannel integration
35:11 Managing E-commerce during the pandemic
40:36 Overcoming crisis through innovation
44:12 E-commerce tech post-pandemic
Find the transcript for this episode and all past episodes at: https://www.unusual.vc/podcast
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and
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Sarah Leary is a Venture Partner at Unusual Ventures, with a focus on Unusual’s consumer practice. Prior to joining Unusual, Sarah co-founded Nextdoor, the free and private social network for neighborhoods. She can be reached at sarah@unusual.vc and
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Michael Krakaris is the co-founder of Deliverr. Prior to starting Deliverr, Michael was a product marketing manager at Symphony Commerce.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.
Further reading from the Startup Field Guide:
Customer Discovery
Building a sales team
Developing your founding insight

Aug 28, 2023 • 34min
How Forward found product-market fit: Adrian Aoun on automating healthcare with AI
Forward is an AI-based healthcare unicorn that combines private doctors with technology to enable data-driven, insurance-free primary care. Forward is now present in 14 cities in the US. In this episode, Sandhya Hegde chats with Adrian Aoun, the founder and CEO of Forward about building a transparent and incentive-driven healthcare system.
Join us as we discuss:
01:47: Forward’s origin story and why Adrian saw the need to reimagine healthcare
04:44: Build an incentive-driven healthcare system
10:05: Approach to building an “MVP”/early clinics
13:51: How Forward thinks about its product roadmap and innovating in healthcare
17:11: How Adrian and his team iterated on early user feedback
20:39: Forward’s approach to productizing healthcare
24:29: The future of AI in healthcare
27:55 How Adrian approached building the early team at Forward
30:51: Advice for founders who are building products with AI
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and
Twitter
LinkedIn
Adrian Aoun is the founder and CEO of Forward. Prior to starting Forward, he founded Wavii, a natural language processing startup acquired by Google. He also worked on special projects for Larry Page at Google.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.
Further reading from the Startup Field Guide:
Starting a company
Iterating to MVP for consumer products

Jul 31, 2023 • 41min
How Sysdig found product-market fit: Loris Degioanni on leveraging open source for cloud security
Sysdig is a cloud native application protection platform that helps stop cloud and container security attacks. In this episode, Sysdig’s founder and CTO, Loris Degioanni chats with Wei Lien Dang about why he founded Sysdig and how he leveraged the power of open source for growth and industry disruption.
Join us as we discuss:
(1:39) How Loris leveraged market and tech stack changes to build Sysdig
(7:46) Sysdig's journey as an early pioneer in containerization technology
(12:16) Sysdig’s pivot from monitoring to cybersecurity
(17:48) The power of open source in building Sysdig
(21:48) The nuances and commitment necessary for a successful open source project:
(28:33) Finding product-market fit in an open source context
(30:42) The role of an open-source project as a brand, marketing tool, and source of lead generation
(31:45) Balancing community involvement and establishing a solid business model
(33:34) Commercializing an open source project
(37:32) Advice for founders building open source companies
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and
Twitter
LinkedIn
Wei Lien Dang is a General Partner at Unusual Ventures and leads investments in infrastructure software, security, and developer tools. Wei was a co-founder of StackRox, a cloud-native security company prior to its acquisition by Red Hat. He can be reached at wei@unusual.vc and
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Loris Degioanni is the founder and CTO of Sysdig. Prior to founding Sysdig, Loris co-created Wireshark, an open source network analyzer.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.
Further reading from the Startup Field Guide:
Starting an open source company
Developing open-source software customers
Building GTM for an open source company

Jul 17, 2023 • 51min
How Gretel found product-market fit: Ali Golshan on unlocking synthetic data for developers
Gretel is a synthetic data platform that allows developers to generate artificial data sets with the same characteristics as real data so they can test AI models without compromising sensitive customer information or privacy. Gretel has a community of over 75,000 developers working with accurate, synthetic data.
In this episode, Sandhya Hegde and Weil Lien Dang chat with Ali Golshan, CEO and co-founder of Gretel about the company’s path to product-market fit.
Join us as we discuss:
(1:48) Ali’s background in US Intelligence and how it shaped his approach as a founder
(3:17) The founding insight that led to the creation of Gretel
(6:35) Ali and his co-founders’ “why now” for building a privacy engineering product
(8:15) Why Gretel decided to focus on developers
(10:47) How Ali and his co-founders narrowed in on early use cases
(15:55) The industries where Gretel found early adopters
(20:20) How Gretel anticipated and adapted to increasingly popular AI models
(27:24) Why Gretel decided to create a multimodal platform for synthetic data
(29:18) The reasoning behind building Gretel GPT
(31:48) How Gretel’s co-founders work together to adapt to the changing tech landscape
(38:05) What Ali sees as the key drivers for adoption within traditional enterprise companies
(40:19) Why they built their ICP around the developer cloud stack
(45:45) Advice for early-stage founders currently building in AI
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and
Twitter
LinkedIn
Wei Lien Dang is a General Partner at Unusual Ventures and leads investments in infrastructure software, security, and developer tool. Wei was a co-founder of StackRox, a cloud-native security company prior to its acquisition by Red Hat. He can be reached at wei@unusual.vc and
Twitter
Linkedin
Ali Golshan is the CEO and co-founder of Gretel. Prior to Gretel, Ali was the Co-founder and CTO at StackRox (acquired by Red Hat), and previously the Founder & CTO of Cyphort (acquired by Juniper Networks).
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.Further reading from the Startup Field Guide:
Defining your ICP
Finding early adopters
Finding co-founders

Jul 3, 2023 • 50min
How Instabase found product-market fit: Anant Bhardwaj on automating data processes for the F100
Anant Bhardwaj, Founder of Instabase, discusses the journey to product-market fit. Topics include founding insights, landing major customers, scaling sales, raising a Series B, and advice for early-stage AI founders.

Jun 19, 2023 • 31min
Launching Bright and Early: Naveen Gavini on growing from first mobile engineer to SVP Products at Pinterest
In this episode, we are debuting “Bright and Early” — an Unusual Ventures interview series with early hires at iconic tech companies. You will often hear successful founders share how crucial their first few hires are. These early employees help define the company's culture. They need to be both doers and leaders who can prioritize ruthlessly. They often have an outsized impact on the company and wear multiple hats as the company grows. Finding them and empowering them to be successful is hard.
In this episode, co-hosted by Chris Marty and Rachel Star from Unusual Ventures, we hear from Naveen Gavini, employee #10 at Pinterest who joined the company 11 years ago as a mobile engineer and went on a career-defining journey to become their head of product.
This conversation covers
(2:06) Why Naveen wanted to join Pinterest and how he got connected to the team
(4:38) What his interview process looked like
(7:07) The key drivers that motivated him to accept the offer
(9:37) Naveen’s first year as an engineer at Pinterest
(12:41) How Naveen brought the team together to build Pinterest’s mobile app
(15:09) How he thought about managing his career path within the company
(18:06) His approach to team-building
(21:04) Pinterest’s interdisciplinary culture of “knitting”
(24:15) Interviewing early hires, specifically for culture fit
To get notified for new interviews in the Bright and Early series, subscribe to our newsletter: https://bit.ly/2VKvTTD
To stay up to date, follow us on:
LinkedIn: https://www.linkedin.com/company/unusualventures/
Twitter: https://twitter.com/Unusual_VC
Chris Marty is an Operating Partner at Unusual Ventures and partners with founders to build high-performing early teams. He can be reached at chris@unusual.vc and
LinkedIn: https://www.linkedin.com/in/christhomasmarty/
Twitter: https://twitter.com/_chrismarty
Rachel Star is Principal at Unusual helping to build and support the firm’s consumer investments. She can be reached at rachel@unusual.vc and
Linkedin: https://www.linkedin.com/in/rachel-star-2948b288/
Twitter: https://twitter.com/rachel_a_star
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to help founders find product-market fit and build iconic software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.

Jun 5, 2023 • 49min
How Weights & Biases found product-market fit: Lukas Biewald on dev-focused ML ops
Lukas Biewald, CEO of Weights & Biases, shares insights on building a developer-focused MLOps platform. Topics include early design partners, user feedback, growth tactics, and leadership tips for AI-native products. Sandhya Hegde from Unusual Ventures leads the conversation.