Casey Winners is a well-known figure in the growth and product community, having worked with or advised companies like Pinterest, Reddit, Canva, Airbnb, Tinder, Thumbtack, GrubHub, and many more. He recently led product at Eventbrite for about three years and is now exploring new opportunities while advising full-time. In this podcast episode, he discusses various topics, including the zero interest rate phenomenon, effective product management, network effects, and more.

Casey is currently working on some long-term Marketplace strategy and growth strategy for Eventbrite, as well as doing some Angel Investing and advising startups in marketplaces and Tech debt as a service. He is also revamping the product strategy program for reforge. Casey is open to helping companies and loves talking to startups.

The CPO role is challenging as it is hard to keep product-market fit within a company for a long time, and the needs of the business shift over time. Any misstep or mistake can blow up in a major way, and frequently CEOs have visions that can change and get misaligned with the product leader.

As a CPO, it is important to prioritize the overall business and create the perception that you care about sales, marketing, and other areas. It is also crucial to diagnose the strengths and weaknesses of your team and product, communicate them clearly with peers, and work towards achieving the goals. Additionally, conducting deep dives and explaining the product to the executive team can help them understand it better.

The product manager noticed that the environment in which many product managers have come up is distorted, and they tend to talk about research instead of shipping to learn. They forgot that the fastest way to learn is to ship.

Common Frameworks and Best Practices The author discusses how new product team members often focus too much on following the "right" way of doing product management and using frameworks, rather than taking risks and using their own creativity to add value to customers. The author also emphasizes the importance of understanding that frameworks are tools to be used when relevant, not strict guidelines to always follow.

The Zero Interest Rate Phenomenon and Advice for Product Managers The author explains how the zero interest rate phenomenon has allowed startups to operate like public companies with unlimited resources, but this will change in the future. The author advises product managers to focus on adding value to customers and the business, rather than just following frameworks, and to seek out companies where they can learn quickly and try new things. The author also encourages product managers to speak up and take risks, rather than censoring themselves or following a strict process.

The decision of when to invest in research depends on the type of job and customers. For consumer products, research is brought in when the impact seems confusing, while for Enterprise, research is done directly with the customer and sales team. For companies in the middle, research is focused on high leverage areas where there is a big problem that is not well defined or where the solution is uncertain. The best researchers know when research is not needed and have enough information.

Whatnot is a live streaming marketplace that focuses on the collectibles market where sellers can go live on video and show their products to potential buyers who can engage with them and bid on different items, making it a combination of Twitch and eBay.

Casey takes a contrarian approach to interviewing product managers, focusing on real scenarios and assessing how candidates would approach them rather than asking about their work history or prepared answers. The goal is to see how well candidates can do the job they are being hired for.

During interviews, the speaker looks for red flags such as lack of research, solutions that take a long time to implement, and not considering the metrics to improve. The speaker also thinks that their importance or awareness in the community is overestimated.

The speaker believes that the real PM job is unlikely to be replaced by AI because it requires subject matter expertise and making good decisions for the company and customers. However, they caution against using AI in the current iteration of the cycle for PMs as it is a tool trained on sounding smart rather than always being smart. They suggest using AI for tedious work that is not the PM's specialty, such as formatting or getting zappier integration to work.

Founder intuition vs. team expertise Founders have built up intuition about their customers and business that are hard to explain to others, so they need to direct their team until they show they've got it. As the company scales, the founder's expertise becomes less relevant, and team expertise goes up.

Pushing back as an employee If you're an employee at a company with a founder who believes they have all the answers, you need to understand that it's their company and they can run it any way they want. If you state your point and are refuted, you need to find ways to be contrarian and prove you're right, whether it's through an experiment, the right customer intro, or the right external advisor. If they still rebuke you, you need to disagree and commit or find a new company to join or start your own.

The founders of Grubhub came up with the idea of building an app for delivery drivers, but the narrator was initially skeptical about its adoption. However, in the long run, it proved to be necessary to have parity with other services like DoorDash and Postmates. The adoption of the app was low initially, but they leveraged restaurant authority to push their drivers to adopt it.

direct, cross-site, and data. Most social networks start as direct network effect businesses but eventually become cross-site and/or data network effect businesses. Adding additional network effects can be a great form of defensibility for businesses.

Zillow's ability to provide real-time pricing information on the value of homes creates a much stickier product for both buyers and sellers, making it a successful innovation that other real estate listing sites have failed to replicate.

Grubhub's Network Effect Disruption Grubhub's network effect was disrupted by DoorDash and Uber Eats, who expanded their selection of restaurants and built heavily managed marketplace models. Grubhub's asset light marketplace model was no longer comprehensive, and they faced disruption pressure from operationally intensive negative margin delivery services.

Grubhub's Response and Lessons Learned Grubhub tried to copy the approaches of DoorDash and Postmates, but it was too late. They could have acquired DoorDash early on, but it would have been risky and investors may have hated it. Grubhub assumed the disruptor was wrong, but they should have assumed the disruptor was right and based their strategy on them playing an optimal game. The lesson learned is to overreact during existential threats and assume the disruptor is right.

The takeaway is to not underestimate the competition, even if their business model seems flawed, as the market will find a way to make it profitable. To compete with established companies like DoorDash or Uber, startups need to focus on a different angle and be incredibly clever, as attacking with a war chest is not enough. Some startups are trying to do white label delivery for restaurants, but they may struggle to be multi-hundred million dollar revenue businesses.

SaaS adding marketplace and vice versa The strategy of adding a marketplace or a SaaS tool to a business model is a popular concept among founders. However, it is more successful for marketplaces to add a SaaS tool than the other way around. The success of this strategy depends on having a direct relationship with customers and a need for transacting with more than one supplier on the supply side.

Examples of successful SaaS and marketplace transitions Eventbrite is an example of a SaaS tool that is transitioning to a marketplace model, which is a challenging process. Fair, on the other hand, is a marketplace that added a SaaS tool and has grown quickly. The success of this strategy depends on having a direct relationship with customers and a need for transacting with more than one supplier on the supply side. The key to success is unlocking cross-side network effects that make it easier to grow.

The primary value proposition of a marketplace is to bring extra business by driving demand to supply. However, some businesses like Patreon and Substack, which wanted to be a marketplace, found that people were not looking for more artists or newsletters to subscribe to. Substack has been able to abstract the idea and provide relevant articles to readers, which has resulted in a wild network effect. Although it may not be worth calling it a marketplace, 80% of new sign-ups are coming from Substack's network.

Consumer subscription startups are harder to build into thriving businesses compared to B2B SAS due to their less predictable nature, worse retention rates, and lack of net dollar retention characteristics. To succeed, B2C subscription startups need higher user-based retention rates, which can be achieved through massive op-x and economies of scale, network effects, or bespoke growth loops. Startups should focus on building organic growth loops or network effects into their business to avoid relying solely on paid acquisition.

"The Goal" by Eliyahu M. Goldratt, "Thinking Fast and Slow" by Daniel Kahneman, and "Profit from the Core" by Chris Zook. He also mentions his favorite recent TV shows and movies, such as "Party Down," "The Last of Us," and "Kicking and Screaming." Casey talks about the importance of cross-functional teams and alignment in product development and recommends designating a driver to make decisions. Finally, he shares his current music favorites and invites listeners to reach out to him on his blog or Twitter.