Class 10: September 17, 2026 · ENTR 5500
Notes from September 17, 2026. These notes record the discussion and instructions given that day. For current requirements and due dates, use the assignment guidelines and semester schedule.
What to take from today
We concluded Frank Addante’s story, opened Apple’s Core through the lens of trust, and turned entrepreneur selection into a concrete group-project commitment. The slides contain the case timeline and the three Rs—roles, relationships, and rewards. These notes emphasize the discussion around them.
Clear communication is entrepreneurial work
An interested contact is not yet a confirmed interview subject. Memorialize an important verbal agreement: send a short written recap and ask the other person to affirm it. This gives both parties a shared understanding of the commitment and a record to return to if plans change.
For the entrepreneur project, obtain written confirmation of three things:
- They agree to participate.
- They can contribute roughly one to two hours total, including coordination and interviews, between now and the first week of November. The working expectation is one or two interviews of about 30 minutes; fuller project guidance is forthcoming.
- They understand that the project will be shared within the class, and can review presentation materials containing their company information before those materials are presented. They need not disclose particular financial or operational details.
Post the confirming email PDF or text screenshot as a reply in your group’s pinned entrepreneur-profile thread on Slack. @mention John on that upload message so he knows it is ready to review. If you plan to record an interview for note-taking, explain the recording and intended use to the interviewee beforehand.
When a group is still choosing, contact plausible candidates in parallel. Assign an owner and response deadline to each outreach, decide how to choose if several people agree, and set a fallback if nobody responds. A useful interview subject needs relevant founding experience and enough recall to discuss concrete decisions—not simply an impressive current title.
StrongMail: decisions have human and structural sides
StrongMail needed enterprise sales expertise. One early hire did little; another treated prospective business as though it were closed. A good résumé cannot replace execution, honest reporting, or fit with the company’s stage.
Enterprise sales usually means a complex sale to a large organization: more stakeholders, integration requirements, scrutiny, and a longer decision cycle. The tradeoff is potentially larger, more durable contracts. The same difficulty that slows initial adoption can make it harder for a competitor to displace an established provider. Think in terms of the customer’s buying process, not a universal employee-count cutoff. Further explanation.
At StrongMail’s decision point, Frank’s preferred sales leader conflicted with Sequoia’s recommendation. Students could make reasonable arguments for trusting his firsthand experience, accepting outside expertise after repeated hiring failures, or testing both candidates. Frank ultimately hired both with distinct territories; the case’s epilogue reports that the approach succeeded and his preferred candidate became the sole VP.
The transferable lesson is to design a decision around evidence, incentives, relationships, and boundaries. The outcome does not establish a rule to always trust your gut or always hire two people. Consider what a founder knew at the time, the pressure they faced, and how their choice affected investor confidence.
Financing and opportunity discovery
Venture capital seeks unusually large outcomes across a risky portfolio. General partners manage the fund and investments; limited partners supply committed capital. In the simplified classroom example, if nine equal investments return nothing, a tenth returning ten times its investment only restores the portfolio’s original capital before fees and other costs. That explains why a sound, profitable business may still be a poor fit for VC.
The bank-versus-VC comparison was about incentives: borrowing brings repayment obligations; equity funding gives investors a share of the upside and may bring influence over company decisions. Neither is automatically the better choice. Accel’s early Facebook investment illustrated the possibility of an outlier return; the precise historical return estimate is not needed for the lesson. Accel’s Facebook record.
Another opportunity can appear inside the work of building the original idea. StrongMail’s story prompted discussion of an internal tool becoming the more promising business. Slack likewise began as a communication tool used while developing the game Glitch. Keep testing whether the original destination or a newly discovered problem offers the stronger opportunity. Slack’s origin.
Apple’s Core: trust outlasts the amount of money
The opening discussion centered on Jobs, Wozniak, and the Breakout compensation dispute described in the case. The lasting issue was the discovery of deception within a trusted relationship, even after the money itself had become relatively insignificant.
John’s metaphor: trust is the ability to put your weight on something and expect it to support you. In a partnership, that weight includes time, effort, judgment, and reliance on another person’s word. A seemingly small breach can change what someone is willing to entrust to you for years.
We will continue the Apple discussion. An optional related book mentioned in class is David Pogue’s Apple: The First 50 Years.
AI as a way to get unstuck
Brief demonstrations showed two useful habits: revisit a previously unsuccessful prototype as capabilities improve, and refine a vague tool request by supplying actual workflow, budget, and constraints. Challenge an AI recommendation and ask why it fits. Building your own solution also makes you responsible for maintaining it; compare that cost with buying a tool. A convincing prototype still needs accuracy and usability checks.
Dates and next steps
- Thursday, September 17, midnight: Quiz 2 was due in eLC.
- Tuesday, September 22: Have the entrepreneur selected and written confirmation posted in the pinned Slack thread. Come ready for the fuller project overview, theme journals, and continued Apple discussion.
- No additional required reading was assigned in this meeting. An optional rescan of the Apple case through the trust lens may help. The copied agenda’s reading language should not be treated as a new assignment.
- Thursday, September 24: Group-project work day. Spend a class period working with your team; reporting details will be explained Tuesday.
Slack is the communication and collaboration space; eLC remains the place for quizzes and grades. The planned course website is intended to consolidate course resources.