Founder Fridays No. 138
Superhuman’s Onboarding Playbook -- When and How to Bundle Products -- Stop Consuming. Start Doing.
Happy Friday.
This is your last chance to participate in the 2025 Legal Survey and get your personalized benchmarked report.
I know many of you have already participated in the Startup Legal Survey — thank you so much! If you haven't yet, please take three minutes now to complete this anonymous, 18-question survey about legal budgets.
Without industry benchmarks, determining appropriate legal spending is guesswork. Your participation helps establish meaningful standards for all founders. As a thank you, you can receive a custom report comparing your approach to similar-stage companies.
Click below to contribute. Thank you!
Superhuman’s Onboarding Playbook
Human touch beats automation. Despite conventional startup wisdom, Superhuman gained an edge through human-led onboarding instead of rushing to self-serve. This approach allowed the email app to deeply understand customers, triple activation rates, and methodically manufacture evangelists who drove referrals and retention. When it finally transitioned to self-serve, it was designed to be opinionated (showing the best way to use the product), interruptive (commanding attention at key moments) and interactive (building muscle memory through guided action). First Round Review (24 minutes)
When and How to Bundle Products
Bundling can backfire. While product bundling creates customer stickiness and raises switching costs in competitive markets, it's surprisingly risky for companies with high attach rates — customers already happily buying multiple products at full price. The most critical gut checks before bundling include analyzing attach rates (lower is safer), competitive landscape, and customer feedback categorizing each product as "need," "nice-to-have" or "pass." For every 10% discount offered, you'll need progressively steeper attack rate increases to break even — a 30% discount requires 2.5x of the customers to upgrade to maintain revenue. a16z (7 minutes)
Stop Consuming. Start Doing.
Theory won't build your company. While founders drown in Twitter threads and business books hoping to decode the perfect strategy, real success happens through deliberate practice — much like learning an instrument. Reading 100 guitar books without playing a single chord leaves you exactly where you started. Business mastery develops through repetition, failure, adjustment and persistence, not intellectual shortcuts. Every hiring mistake teaches more than reading profiles, every product iteration reveals more than design theories and every customer interaction refines your instincts in ways no framework can capture. Stop consuming content about business and start producing results through action — the difference between thinking about business and being in business is found in the doing. Jason Fried (5 minutes)
Founder FAQ: What’s the Deal with Unpaid Internships?
Free labor costs more than you think. While cash-strapped startups might view unpaid internships as an attractive cost-saving measure, this approach creates substantial legal risks under the Department of Labor's "primary beneficiary test," which requires meeting seven specific criteria. Beyond potential penalties and back pay obligations, unpaid internships systematically exclude talented candidates who can't afford to work without compensation, creating homogeneous talent pools and contradicting any organizational commitment to equity. Research confirms these programs reinforce existing socioeconomic disparities by restricting opportunities to those with financial privilege, ultimately limiting your access to diverse perspectives and innovative thinking — the very elements startups need most. Westaway (7 minutes)
Startup Funding Guides
I’ve put together a series of guides to equip founders to excel at fundraising. These guides break down the deal term-by-term and give you negotiation tips so that you can speak to investors with confidence.
Convertible Note: Guide / Video
Is the Billable Hour Right for Startups?
Most law firms bill startups by the hour because that's the status quo. But while it may work for big companies, the billable hour is likely the wrong model for startups. Why?
It incentivizes inefficiency. Firms are motivated to pad hours rather than work efficiently. This adds unnecessary costs.
It rewards busywork over results. Startups care about outcomes, not hours logged.
Costs are unpredictable. With fluctuating monthly hours, legal spend is hard to budget.
It stifles innovation. Hourly billing gives no incentive to find better solutions. Startups need forward-thinking counsel focused on results. That's why we've ditched the billable hour for transparent flat fees.
If you're ready to explore a law firm with a better billing model, let's talk.
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