46: Melissa Kwan - Bootstrap vs VC, Mastering the startup game
12/16/23 • 61 min
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
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
Previous Episode
45: Chris Tottman & Richard Blundell - focussing your business to success while dreaming big
Chris Tottman and Richard Blundell joined me for a fantastic conversation about how they think from their own operators’ perspective when it comes to investing in successful businesses and their people.
Why you should not talk to investors who never went through the personal pain of failing and why it most of the time comes down to the basics of running a successful business:
- Being obsessed with customers in a narrow market
- Product Market Fit is not just having a great product in a great market but also communicating it where your customers are
Timestamps:
11:00 The origin story of Notion VC, a founder/operator-led fund. An aggregator of fuckups and occasional successes
17:10 Why do we keep making the same mistakes in business?
27:00 Why anyone invests in a business. Metrics to evaluate the present, personality to see the future
33:30 Why should anyone listen to your pitch? When chaos is not avoidable with success
45:20 Are you failing because your market is too big or too small? Dangers of going too broad with your ICPs
53:50 Markets are not just what people want but where they communicate and recommend
Next Episode
47: Jeff Gothelf - OKRs, Humility, and the Real Value of Innovation in Business
Jeff Gothelf, one of the most critical voices around OKRs and being outcome-driven, sat down with me for an hour-long amazing conversation:
We touch on why using OKRS is useless if you can’t admit when you are wrong and be open to feedback from your teams.
How do you set outcome-driven goals for exploratory research and the role of humility in organizational success? Why shipping something does not mean you’re adding value.
Finally, we discuss common failure points in organizations and the future of impactful startups.
Takeaways
- Executives should practice humility and accountability, admitting when they are wrong proactively.
- Setting outcome-driven goals for exploratory research helps determine the value and feasibility of new ideas.
- Common failure points in organizations include a lack of humility, a failure to prioritize the customer, and an overemphasis on the next hottest thing.
Timestamps
00:00 The Power of Humility and Accountability
13:06 The Importance of Putting the Customer First
19:08 Avoiding the Overuse of AI
25:46 Setting Outcome-Driven Goals for Exploratory Research
32:31 The Role of Humility in Organizational Success
43:39 Common Failure Points in Organizations
45:24 The Future of Impactful Startups
Shownotes
Jeff Gothelf: https://www.linkedin.com/in/gothelf/
Jeff’s Website: https://jeffgothelf.com/
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