PRODUCTEA with Leah, Growth & Senior Leadership

Summary

Melissa Kwan, CEO of eWebinar and serial bootstrapper, discusses the challenges and benefits of bootstrapping a business versus seeking venture capital funding. She is the poster child for urging founders to focus on real customer feedback and paying customers without loading up on VC problems.

We discuss the importance of understanding the customer, personal goals and ambitions, the challenges of building and scaling a product, defining success and financial goals, the desire for financial independence, determining the financial number to sleep well, and the value of personal branding and trust.

Takeaways

• Bootstrapping is a lifestyle choice that offers freedom and control over the direction of a business. At the same time, venture capital funding commits a company to a venture-scale outcome and a different lifestyle.
• The future of tech startups lies in vertical SaaS businesses and smaller, niche solutions that cater to specific markets.
• Why demo calls and salespeople are becoming less necessary as self-serve options and efficient onboarding processes become more prevalent.
• Determining the financial number needed to sleep well varies for each individual.
• Personal branding and trust are valuable assets for entrepreneurs.
• Writing and building an audience can lead to new opportunities and connections.

Timestamps

00:00 The Lifestyle Choice of Bootstrapping vs. VC Funding

05:17 The Trajectory of eWebinar's Growth

09:31 The Challenges of VC Funding and the Importance of Profitability

13:51 The Difference Between Media Validation and Market Validation

19:35 The Rise of Vertical SaaS and Lifestyle Businesses

25:46 The Importance of Analyzing Past Behavior to Predict Future Behavior

32:00 The Problem with Demo Calls and the Shift Towards Self-Serve

37:06 Determining Pricing and the Value of Respecting Customer's Time

45:27 Understanding the Importance of Knowing the Customer

46:25 The Challenges of Building and Scaling a Product

47:24 Defining Success and Financial Goals

48:19 The Desire for Financial Independence

50:38 Determining the Financial Number to Sleep Well

55:41 The Value of Personal Branding and Trust

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Leah on Linkedin / Twitter / Youtube

Kyle Poyar joined me on the ProductTea to talk about anything that makes businesses and VCs tick.

I love this conversation for the simplicity of how Investors make decisions and what the future of our industry might very well look like. You should leave this podcast once you listened to it with some great insights into what makes product-led growth companies run differently than their competitors.

00:00 Kyle and Leah’s introduction

04:00 Using LinkedIn to validate concepts and Ideas

07:20 The balancing act of what we say and what we mean in different channels

08:45 Consistency on LinkedIn and challenging established things like the NPS

13:00 Kyle’s “Growth Unhinged” posts as a well of knowledge of the past 6 years in PLG

15:30 The business model of “Openview”, Investment profile, and typical companies to invest in

18:45 How to determine whether a company has reached product-market fit

22:15 How to “show” product-market fit with non-obvious numbers

26:20 How long it takes to “proof” a certain motion, typical Lifetime Value numbers

29:30 The data Gap of tracking emails instead of people

34:57 Investing into companies that have no revenue to show for

39:00 Pre-Seed investment methods

43:33 Do you know how the business you work in, works?

45:00 Putting a price on Customer Success and the increasing business literacy around it

47:30 When risk profiles are driven by greed and how PLG runs on a “skeleton crew”

50:15 Where PLG companies spend more money than others

51:50 Product-Led Sales and the maturity it’s in.

Connect!

Kyles LinkedIn: https://www.linkedin.com/in/kyle-poyar/
Kyle’s Substack:

Kyle Poyar’s Growth Unhinged

Connect with Leah: https://linktr.ee/leahtharin

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Leah on Linkedin / Twitter / Youtube

Summary
Chess.com has grown from being a simple chess service to a thriving 150 million ARR business. The company has focused on making chess accessible to everyone through services around a product that hasn’t changed in centuries.
We touch on the challenges of scaling a company and the role of titles and leadership in an organization and how many times Erik wanted to give up in the process.
Erik talks about the need for passion and love for the product, and the importance of hiring people who align with the company's mission.
Takeaways
Chess.com has expanded its user base beyond the chess community by making chess accessible to everyone instead of just pros.
Titles should not be the focus, and it's more important to hire people who are passionate and aligned with the company's mission more than anything else
Finding a balance between managing the company and staying involved in the product is key for being a CEO at a scale of 500 people and more.
Sound Bites
"Anyone can have a relationship with chess. It doesn't have to be old white guys in suits. It can be all genders, all ages, all races, all countries, all intellectual capacities. Chess is for everyone."
"Chess.com could not only serve the community, but we could grow the game and change the definition of who identifies as a chess player."
"Our next phase as a company is to be an engagement-focused business and drive revenue to invest in building the game and driving cooler media."
"Making money is just the fuel for the mission"
Chapters
15:39 Expanding the Chess Community
30:08 The Role of Growth Teams in Retention and Value Creation
37:03 Understanding User Cohorts and Behavior Tracking
39:21 Driving Revenue Growth Through Churn Analysis
41:29 The Role of Revenue in the Company's Mission
45:02 Using Metrics to Drive Product Improvement
54:04 The Challenges of CEO Responsibilities
01:02:32 Separating Leadership and Management Roles
My Blog / Newsletter: www.leahtharin.com
Linkedin: https://www.linkedin.com/in/leahtharin/
Twitter: https://twitter.com/LeahThar
#productledgrowth

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Leah on Linkedin / Twitter / Youtube

Motivation, forming habits, managing time, and why it’s important to know how much you enjoy solving problems with Jason Fried.
Jason is really special to me and a 2nd time guest. Whenever we go at it, there are two worlds clashing in the best way possible. We are both never content with traditions and challenge the status quo; we just often disagree on how to challenge them while we agree on the first principles behind it all.
Our fight about calendars and time management is one of my favorite moments in the entire history of my podcast.
Takeaways
Real-world experience is the best way to learn and develop skills.
Consistency and finding what works for you individually are key to forming habits.
Calendars can be a useful tool for managing time, but it is important to protect one's time and not let others have too much control over it.
New employees at 37 Signals gain knowledge about the market and customers over time rather than being overwhelmed with information upfront.
Metrics should be used in conjunction with observation and intuition to make informed decisions.
Sound Bites
"The best way to learn is to do the work."
"If I'm putting something off for a long time, it's probably because I'm not motivated to get it done."
"The people you hire are pretty much your most important decisions you're going to make in any business ever essentially."
"At the one year point, we have to basically hire you again. This is how we think about it internally."
Chapters
02:02 Understanding and Harnessing Motivation
04:18 The Importance of Making the Right Hiring Decisions
06:16 Forming Habits: Consistency and Finding What Works
16:31 Managing Time: The Role of Calendars and Protecting Your Time
35:15 The Right Size for a Company vs Scaling
55:09 Measuring Subjective Factors in Product Development
58:53 Using Metrics and Intuition to Make Informed Decisions
Jason’s LinkedIn: https://www.linkedin.com/in/jason-fried/
Jason’s Blog: https://world.hey.com/jason
My Blog / Newsletter: www.leahtharin.com
Linkedin: https://www.linkedin.com/in/leahtharin/
Twitter: https://twitter.com/LeahThar
#productledgrowth

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Leah on Linkedin / Twitter / Youtube

If you spend money on paid ads, chances are that you’re being taken advantage of. The biggest providers do it to you because they can and they optimize their systems more and more towards it.

Rand Fishkin and me discuss the challenges and limitations of paid advertising, the role of AI in marketing, the importance of organic initiatives and why you can’t skip good quality audience research.

Takeaways

• Many marketers spend money on ads that are shown to people who would have converted anyway.
• The best marketing channels are often the hardest to measure. Paid advertising can be limited and may not always provide the desired results because you don’t see how they really perform.

Sound Bites

• "There's lots of people being taken advantage of in the digital marketing and advertising ecosystem today."
• "There are literally hundreds of billions of dollars that flow into that ecosystem that don't necessarily have careful accounting."
• "We're going to need to do these sketchy things that essentially take credit for sales that would have already happened, show people more ad results, reduce the quality of the organic results, make it harder to identify ads, force people to scroll down further, lazy load the organic stuff and quick load the paid stuff."
• "Treat digital advertising the way Coca-Cola treated billboards in 1965. Test different messages and campaigns in specific markets and analyze the lift in same-store sales to determine effectiveness."

Chapters

06:30 The Issues with Digital Advertising

10:22 Taking Advantage of the Digital Marketing Ecosystem

13:14 The Challenge of Proper Accounting and Attribution

18:29 The Misleading Nature of Digital Metrics

23:03 The Difficulty of Measuring the Best Marketing Channels

23:59 The Limitations of Paid Advertising and the Need for Innovation

25:27 The Impact of AI on Marketing and the Changing Web

28:10 The Value of Organic Initiatives in Marketing

29:31 Testing and Experimentation in Marketing

34:13 The Importance of Working with Competent Experts

41:26 The Significance of Qualitative Metrics in Marketing

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Leah on Linkedin / Twitter / Youtube