Why Timely Pivots Matter: Lessons from Startup Failure

"You gotta be able to say, OK, what is my target, what are my goals, and... be really honest about achieving them... maybe it's time that we go... in a different direction, or we shut down or we look for a buyer..."

• Regularly assess if you're meeting your targets.
• Be willing to make difficult decisions to pivot or exit.
• Clear goals help in evaluating progress objectively.

"Their priorities are not always what their customers... if you look at a student as a customer... And so really being honest with yourself about is what I'm building aligning with who ultimately is writing the check."

• Recognize that large enterprises may not prioritize innovation.
• Align your offering with their core business priorities.
• Be prepared for longer sales cycles and structural barriers.

"We tried it out, um, in a very janky hacky way... we saw it's actually starting to work and engagement was going up..."

• Use quick prototypes to test core functionality.
• Validate assumptions without extensive development.
• Focus on user engagement before perfecting the product.

"Try to push for buy, like, get them to pay, like, hey, listen, if you're not gonna pay, it's obviously not that important to you... stop trying to think that... determination...they emerged with like 50 millionaire... that rarely rarely happens."

• Early revenue confirms customer commitment.
• Avoid prolonged efforts without financial validation.
• Focus on signals that indicate real market demand.

"Understand the structure of your market... their priorities are not always what their customers... if you look at a student as a customer... And so really being honest with yourself about is what I'm building aligning with who ultimately is writing the check."

• Align your product with the priorities of decision-makers.
• Recognize that end-users and buyers may have different priorities.
• Deeply study your market to avoid misalignment.

"I could have... integrated large language models into the peer to peer sessions... But by then it was like, I was so burnt out... Now there's this new technology, OK, let's try another year to try to figure this out."

• Incorporating AI requires readiness and resources.
• Late adoption may not be feasible due to burnout or resource constraints.
• Stay updated on technology trends to remain competitive.

"We pivoted into other areas, but we pivoted, quite frankly, into a different market... there wasn't anything that really jumped out at us as being really exciting, and we thought could create a big... market."

• Assess excitement and potential in your current market.
• Pivoting may involve entering entirely new markets.
• Ensure the new market aligns with your expertise and resources.

"They basically said don't charge the schools anything like you're effectively building a marketplace, like keep getting the product right... And they said, don't worry about monetization right now. Like, just make it so good that they can't ignore you."

• Advisors may suggest delaying monetization to focus on user growth.
• Consider the trade-offs; lack of revenue can hinder validation of PMF.
• Balance product development with testing willingness to pay.

"I basically said, OK, what's a good starting point? Where are my relationships today where I could potentially get distribution. And started there, and he agreed to try it out."

• Use personal networks to access initial users or customers.
• Early supporters can provide valuable feedback and credibility.
• Starting with warm leads accelerates product validation.

"But I realized that... whatever vision or product we were building wasn't resonating with the economic buyer... The students loved what we were doing, right? But the economic buyer had different set of priorities."

• Charging customers early validates demand and alignment with the buyer's priorities.
• Relying on user enthusiasm without buyer commitment can be misleading.
• Align your product with those who ultimately write the check.