Hey y’all — here’s today at a glance:
Opportunity → Expert AI Sales Agent
Framework → PESTLE Analysis
Tool → Kick
Trend → Outcome-Based Selling
Quote → Don’t Let Bad Reasons Stop You
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🔗 Houck’s Picks
My favorite finds of the week.
Fundraising
Aditya Singh shares the founder ownership % after each funding round (Link)
Martin Tobias shares what founders don’t have that he makes bets on (Link)
Growth
Jake Castillo on the type of trust that converts (Link)
ICYMI
Level up your workflow for Q3 with 25% off Google Workspace (Link)*
Starter Story shares the 24 startups he tried to build & why they failed (Link)
Jared Friedman on how to find a truly impactful idea (Link)
💡 Opportunity: Sales Reminder Agent
Sometimes you just need a little nudge.
That’s at least what Adam Wazzan, co-founder of orchid.ai (which went through YC last year) thinks:
A simple agent that bumps you in Slack or over iMessage, WhatsApp, or email to follow up with someone is probably more useful and timely than whatever system you’re using to set reminders right now.
An interesting observation here: even agents with seemingly small, discrete tasks still need a ton of context and access to be able to do their jobs well.
To me, that implies that the future (where we all have tons of agents working for us, managing each other, etc) will require robust permissions and access controls, and the traditional software platforms that there are likely many more opportunities in the MCP space too.
🧠 Framework: PESTLE Analysis
Startups are fragile and not everything is within your control.
Macro factors can materially shift your chances of success, and you simply have to be adaptable to them.
PESTLE is a framework that describes the types of risks to look for:
Political → Leadership changes, taxes, and trade rules. Look for policy risks before expanding or entering regulated markets.
Economic → Inflation, spending, interest rates, and costs. Assess customer affordability, pricing power, and fundraising timing.
Social → Attitudes, demographics, and culture. Align your messaging with real trends.
Technological → Innovation, adoption, and access. Inform your product choices and pivot to new approaches when needed.
Environmental → I’d consider this one a bit more optional for most industries, but you can look for sustainability-focused edges where it makes sense to.
Together, you’ll have a good handle on external factors if you review these monthly or quarterly.
🛠 Tool: Kick
If bookkeeping is the task you keep pushing to "future you," it's worth taking a look at Kick.
Kick is an AI-powered bookkeeping platform that automatically categorizes transactions, matches receipts, reconciles accounts, and generates real-time financial reports. It connects with banks, Stripe, PayPal, Gusto, Ramp, and thousands of other financial institutions.
If you're a founder, freelancer, consultant, or small business owner who wants cleaner books without the usual bookkeeping headaches, try Kick.
📈 Trend: Outcome-Based Selling
Still charging by seat? Or by tokens used?
Your customers probably wish you weren’t.
Increasingly, companies that charged based on the number of positive outcomes they achieve for their customers (i.e. booked meetings, impressions generated, etc) are being preferred by those customers.
The reason is simple: it fundamentally de-risks a customer’s purchase since, really, would you rather pay to consume (and hope the results work out and deliver real value) or pay per result?
Here are some reasons it generally makes more sense:
Risk is assumed by the vendor, not the customer
Cost aligns with actual business value generated
The vendor has a stronger incentive to perform
Customers get a more clear map of CAC to LTV
Honestly, it also is kind of a flex. If a vendor has outcome-based pricing, it makes customers feel confident that they know what they’re doing.
If you’ve tried outcome-based pricing for your startup, I’d be curious to know how customers have responded… shoot me a reply and let me know.
💬 Quote: Don’t Let Bad Reasons Stop You
Founders can’t afford to be defeatists.
Many successful startups have been built on top of the graves of others that tried something very similar. For example, Instacart is worth $10 billion while Webvan crashed and burned.
There are reasons why things fail, of course.
In Webvan’s case it was a combination of excessive burn, market conditions (aka the dotcom crash), and it being too early for the tech to really solve what it tried to.
My point is that even if someone’s failed before, or the market’s crowded, those are among the many bad reasons to assume you’ll fail.
Assess the opportunity objectively. Do you have a unique way to acquire users/customers, retain them, or some other defensible and actually disruptive reason why you will win?
If so, that’s all that matters.
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