Startup Field Guide by Unusual Ventures: The Product Market Fit Podcast

Co-Founder of Webflow, Bryant Chou, discusses the company's journey to success, including organic marketing strategies, lessons from their private beta, and finding product-market fit. They also touch on Webflow's product roadmap and team building.

Christina Cacioppo, CEO and co-founder of Vanta, shares insights from her journey in automating security compliance for startups. She discusses overcoming the daunting SOC2 certification process and achieving product-market fit. Christina emphasizes the importance of customer engagement and iterative sales strategies. She also explores leadership growth in a fast-evolving environment and the role of mentorship in developing management skills. Her advice for seed-stage founders highlights building a solid foundation before seeking venture capital.

The SQL database that sits under most applications in the world is old technology that was not built with the Cloud in mind. Now we live in a Cloud-Native world and it's important for developers to have a database that offers the same guarantees as legacy SQL database technology while also taking advantage of life in the cloud. Listen in as Peter Mattis Co-founder and CTO at Cockroach Labs talks about the cloud-native, distributed SQL database that provides next-level consistency, ultra-resilience, data locality, and massive scale to modern cloud applications. Join us as we discuss: What were the unique insights that Peter and his team felt that drove them to creating a new database Why open source was a sensible approach for Peter and his team to take in terms of strategy Who were the early adopters of the open source project and Peter's advice to first time founders to be able to engage and foster a small community of users How Peter built his team early on to answer the technical problems that came with building a database     About Unusual Ventures — Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building infrastructure software and application-level companies. Unusual was founded in 2018 with the mission to reinvent the venture capital engagement model by serving entrepreneurs with an unprecedented level of hands-on services. Described as a partner versus a top-down stakeholder by its portfolio companies, Unusual is laser-focused on serving exceptional founders and teams building innovative products. With offices in Menlo Park, San Francisco, and Boston, Unusual has invested in category-defining companies like Arctic Wolf Networks, Carta, Robinhood, Harness, and Vivun. About Sandhya Hegde — Sandhya is a General Partner at Unusual Ventures, leading investments in enterprise SaaS companies. Previously an early employee and executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and on Twitter (https://twitter.com/sandhya) and LinkedIn (https://www.linkedin.com/in/sandhyahegde/).  Further reading: How to stand out in an established open-source community: https://www.field-guide.unusual.vc/field-guide-enterprise/stand-out-in-an-open-source-community  How to pick the right GTM motion to reach $100M ARR: https://www.field-guide.unusual.vc/field-guide-enterprise/picking-a-gtm-motion  How Cockroach Labs leveraged open source to find product-market fit: https://www.unusual.vc/post/cockroach-event  Free plan vs. free trial in PLG: https://www.field-guide.unusual.vc/field-guide-enterprise/free-plan-vs-free-trial 

In today's episode, we hear from Andy Rachleff, who coined the term “product-market fit” which served as the inspiration for this podcast. Andy Rachleff is a legendary Venture Capitalist who originally coined the term "product-market fit." Andy has had an incredibly accomplished career in the tech industry, co-founding Benchmark Capital in 1995 and Wealthfront in 2008. Andy has mentored and guided hundreds of founders and investors, and in this episode talks about why understanding product-market fit is the only thing that matters and all the pitfalls founders face along the way. Join us as we discuss: How Andy got into venture capital and ended up starting Benchmark Who and what inspired Andy to coin the term product-market fit The core concepts behind product-market fit and why it’s the only things that matters for founders and investors What truly defines an MVP and how it should test the desperation hypothesis About Unusual Ventures — Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building infrastructure software and application-level companies. Unusual was founded in 2018 with the mission to reinvent the venture capital engagement model by serving entrepreneurs with an unprecedented level of hands-on services. Described as a partner versus a top-down stakeholder by its portfolio companies, Unusual is laser-focused on serving exceptional founders and teams building innovative products. With offices in Menlo Park, San Francisco, and Boston, Unusual has invested in category-defining companies like Arctic Wolf Networks, Carta, Robinhood, Harness, 
and Vivun. About Sandhya Hegde — Sandhya is a General Partner at Unusual Ventures, leading investments in enterprise SaaS companies. Previously an early employee and executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and on Twitter (https://twitter.com/sandhya) and LinkedIn (https://www.linkedin.com/in/sandhyahegde/). Further reading: Building conviction in a startup: https://www.field-guide.unusual.vc/field-guide-enterprise/building-conviction Customer validation: going from idea to sellable product: https://www.field-guide.unusual.vc/field-guide-enterprise/pmf-customer-validation What are design partners, and how do you acquire the right ones? https://www.field-guide.unusual.vc/field-guide-enterprise/picking-design-partners 12 tips to improve your MVP with early adopters: https://www.field-guide.unusual.vc/field-guide-enterprise/shape-your-mvp-with-design-partners

Early revenue can sometimes fool you into thinking that you have product-market fit. Startups begin to focus on growth without having solved the core problem their customers are playing them to address. In this episode, we are joined by Lars Albright, a General Partner at Unusual Ventures, where he leads investments in vertical SaaS and fintech startups. Lars is a three-time founder of enterprise software companies, having sold two of his companies to Apple and Mastercard. Today, Lars joins us to talk about his last startup SessionM, a pioneer in mobile loyalty, and even today, powers the loyalty infrastructure for Fortune 1000 brands. Join us as we discuss: How SessionM needed to find product-market fit with 3 different customer stakeholders The launch of mPlus Rewards and early traction Why Lars and his team decided to pivot from coalition loyalty programs to enterprise software despite the revenue traction The challenges of working with fortune 500 companies as a small startup and the lessons Lars took from that time Lars’ advice to founders who have revenue but not product-market fit   About Unusual Ventures — Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building infrastructure software and application-level companies. Unusual was founded in 2018 with the mission to reinvent the venture capital engagement model by serving entrepreneurs with an unprecedented level of hands-on services. Described as a partner versus a top-down stakeholder by its portfolio companies, Unusual is laser-focused on serving exceptional founders and teams building innovative products. With offices in Menlo Park, San Francisco, and Boston, Unusual has invested in category-defining companies like Arctic Wolf Networks, Carta, Robinhood, Harness, 
and Vivun. About Sandhya Hegde — Sandhya is a General Partner at Unusual Ventures, leading investments in enterprise SaaS companies. Previously an early employee and executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and on Twitter (https://twitter.com/sandhya) and LinkedIn (https://www.linkedin.com/in/sandhyahegde/). Further reading: Customer validation: https://www.field-guide.unusual.vc/field-guide-enterprise/pmf-customer-validation Lars’ core fintech themes and advice for founders in today's market: https://www.unusual.vc/post/core-fintech-themes-and-advice-for-founders-in-todays-market Loyalty 3.0: Where consumers become owners: https://www.unusual.vc/post/loyalty-in-a-web3-world

Successful startups need to solve a problem, but there is a big difference between a founder knowing a problem exists in the abstract and a founder experiencing the pain points firsthand and developing ways to solve it. Laura Behrens Wu is the Founder and CEO of Shippo, a shipping platform designed to give every merchant access to the best-in-class tools and technology reserved for retail giants. Over 100k brands trust Shippo to ensure their customers love how their products are delivered. In this episode, Laura takes us through the product-market fit journey of Shippo and her journey of evolving as its CEO. Join us as we discuss: The origin story of Shippo when Laura first launched the company in 2014 How Laura approached the path to find product-market fit Shopify app vs API company - solving the chicken and egg shipping problem How the pandemic affected Shippo and what it was like making decisions amid all the chaos happening in the logistics and supply chain industry How Laura invested in herself as a founder and CEO About Unusual Ventures — Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building infrastructure software and application-level companies. Unusual was founded in 2018 with the mission to reinvent the venture capital engagement model by serving entrepreneurs with an unprecedented level of hands-on services. Described as a partner versus a top-down stakeholder by its portfolio companies, Unusual is laser-focused on serving exceptional founders and teams building innovative products. With offices in Menlo Park, San Francisco, and Boston, Unusual has invested in category-defining companies like Arctic Wolf Networks, Carta, Robinhood, Harness, 
and Vivun. About Sandhya Hegde — Sandhya is a General Partner at Unusual Ventures, leading investments in enterprise SaaS companies. Previously an early employee and executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and on Twitter (https://twitter.com/sandhya) and LinkedIn (https://www.linkedin.com/in/sandhyahegde/). Further reading: Customer validation: https://www.field-guide.unusual.vc/field-guide-enterprise/pmf-customer-validation The Unusual Guide to pre-seed: https://www.field-guide.unusual.vc/field-guide-enterprise/building-conviction CEO/founder prioritization template: https://www.field-guide.unusual.vc/field-guide-enterprise/leadership-ceo-and-founder-prioritization Leading through uncertainty: https://www.field-guide.unusual.vc/field-guide-enterprise/leadership-through-crisis

Since the rise of COVID-19, every company has adopted remote work, and our guest's mission is to create a more equal world by making it possible for talented professionals to work from any country they choose to. Tony Jamous is a serial entrepreneur and the founder of Oyster, a global employment unicorn that helps companies hire employees and contractors anywhere in the world. Before Oyster, Tony was the founder of Nexmo (2010), a Twilio competitor that was acquired by Vonage in 2016 for $230M. In this episode, Tony takes us through the product-market fit journey of Oyster. Join us as we discuss: The origins of Oyster in April 2020 as world implemented lockdowns Tony's approach to product-market fit and the milestones and key metrics that gave them confidence that they found it The learnings that Tony took from his first company Nexmo, to help him build Oyster The challenges of creating connection across a remote team and how Oyster uses Kona Tony's best advice for seed stage founders just starting out on their journey  About Unusual Ventures — Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building infrastructure software and application-level companies. Unusual was founded in 2018 with the mission to reinvent the venture capital engagement model by serving entrepreneurs with an unprecedented level of hands-on services.  Described as a partner versus a top-down stakeholder by its portfolio companies, Unusual is laser-focused on serving exceptional founders and teams building innovative products. With offices in Menlo Park, San Francisco, and Boston, Unusual has invested in category-defining companies like Arctic Wolf Networks, Carta, Robinhood, Harness, 
and Vivun. About Sandhya Hegde — Sandhya is a General Partner at Unusual Ventures, leading investments in enterprise SaaS companies. Previously an early employee and executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and on Twitter (https://twitter.com/sandhya) and LinkedIn (https://www.linkedin.com/in/sandhyahegde/). Further reading: Managing remote teams: https://www.field-guide.unusual.vc/field-guide-enterprise/leadership-managing-remote-teams Key metrics for product-led SaaS (from SaaStr 2022): https://docs.google.com/presentation/d/1CT34wM2QSVhNErZ_5tB-VMv_OCREwM4vdJ20PfbLIIo/edit#slide=id.g13acbf38164_0_86  Leading through uncertainty: https://www.field-guide.unusual.vc/field-guide-enterprise/leadership-through-crisis

While some startups experiment and pivot their way into product-market fit, others have founders with a unique insight that needs persistence. After a rough  6 year start as a company between 2012-2018, Arctic Wolf hit a tipping point driven by market awareness. In the past 4 years, the growth rate of the business has been phenomenal. Founder Brian NeSmith joins us to discuss his conviction to keep going and how he kept his talented team together even when results weren't what they expected. Brian NeSmith is a cybersecurity industry veteran, having led three successful companies - the latest of which is Arctic Wolf Networks. Last valued at over $6BN, Arctic Wolf is the leader in the cybersecurity category known as MDR - Managed Detection and Response, provided as a service. In this episode, Sandhya is joined by co-host John Vrionis, her partner and founder of Unusual Ventures. John led the first venture investment in Arctic Wolf, a $7.5M round by Lightspeed when Brian first started the company. Join us as we discuss: The origin story of Arctic Wolf and why John backed Brian Brian’s framework for evaluating market demand and product-market fit Brian's approach to fundraising in 2017-18, when the 150+ investorshe pitched were concerned by AWN’s story as well as a market crash, and how John supported Brian during this time How Brian handled tough board conversations when times were hard, and what John saw Brian do well as a CEO managing the board Brian's advice for founders on quitting or pivoting away from an idea   To learn some of the skills Brian and John discussed, explore the Field Guide modules on: Raising a Seed or Series A round Managing a Series A board meeting CEO/Founder prioritization Leading through uncertainty   About Unusual Ventures — Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building infrastructure software and application-level companies. Unusual was founded in 2018 with the mission to reinvent the venture capital engagement model by serving entrepreneurs with an unprecedented level of hands-on services. Described as a partner versus a top-down stakeholder by its portfolio companies, Unusual is laser-focused on serving exceptional founders and teams building innovative products. With offices in Menlo Park, San Francisco, and Boston, Unusual has invested in category-defining companies like Arctic Wolf Networks, Carta, Robinhood, Harness, 
and Vivun. About Sandhya Hegde — Sandhya is a General Partner at Unusual Ventures, leading investments in enterprise SaaS companies. Previously an early employee and executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and on Twitter (https://twitter.com/sandhya) and LinkedIn (https://www.linkedin.com/in/sandhyahegde/).

StackRox is a security startup born in 2015. After many initial setbacks, StackRox went on to become a leader in container security, riding the Kubernetes wave and helping cloud-native companies secure their software. Wei Lien Dang joins us today to discuss how StackRox found product-market fit.   Wei Lien Dang is a General Partner at Unusual Ventures. Before joining the venture capital firm, Wei was the Co-Founder of StackRox. StackRox became one of the first startups in the container security world to offer a Kubernetes-native solution and in 2021, was acquired by Red Hat.   Join us as we discuss: What drew Wei to StackRox and his transition from being a product executive to a founder? StackRox’s product-market fit journey and the indicators that they had found product-market fit after their pivot.  How did StackRox define its product strategy? How StackRox leveraged open source as a critical part of its go-to-market strategy and Wei’s advice for founders going open source. About Unusual Ventures — Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building infrastructure software and application-level companies. Unusual was founded in 2018 with the mission to reinvent the venture capital engagement model by serving entrepreneurs with an unprecedented level of hands-on services. Described as a partner versus a top-down stakeholder by its portfolio companies, Unusual is laser-focused on serving exceptional founders and teams building innovative products. With offices in Menlo Park, San Francisco, and Boston, Unusual has invested in category-defining companies like Arctic Wolf Networks, Carta, Robinhood, Harness, 
and Vivun. About Sandhya Hegde — Sandhya is a General Partner at Unusual Ventures, leading investments in enterprise SaaS companies. Previously an early employee and executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc and on Twitter (https://twitter.com/sandhya) and LinkedIn (https://www.linkedin.com/in/sandhyahegde/).

Henry Ward, Co-Founder and CEO of Carta, talks about scaling their startup to product-market fit. They discuss building products designed for distribution, early go-to-market lessons, why they didn't start with self-serve, and changing pricing model without upsetting customers.