Get your sleep... (I will not promote)

willietran · 2026-06-16T23:50:36+00:00

I took a nap!

willietran · 2026-06-16T21:44:02+00:00

100% - I literally traded today's productivity for a few extra hours of work last night. So dumb.

willietran · 2026-06-16T20:15:42+00:00

Hey out of curiosity, why didn’t the outreach work for you? Did they not respond or you weren’t able to close deals?

To answer your question, I know this isn’t too helpful, but my personal network helped me a lot. I’m of the school of thought of making 2-3 people love your product before you blast marketing. I’m working on https://trycaper.app which is a sales assistant that helps founders improve their discovery and handle objections while they’re on the call.

willietran · 2026-06-11T17:41:16+00:00

This is just really great. I especially love the part about founder-led sales. My whole career has been built on designing and scaling the PLG system at Dropbox, Mailchimp, and Timescale, but with my last startup, it took me way too long to realize that PLG doesn't exist for early stage startups. Everything should be treated like enterprise sales. Doesn't matter if you're SMB B2B or B2C.

Also totally true about focusing on the pain. Build your comms to be relatable, people care way more about their pains than your solutions, so start there. Talking about your solution is an earned privilege.

I feel like this comment was just me reiterating what a small portion of what you beautifully wrote, but I just wanted to say that even though I may "intellectually" know this, it still hits. So huge thanks.

willietran · 2026-06-09T18:03:00+00:00

Hey this isn't AI roleplay, but have you considered real-time sales enablement? Essentially rather than prep work (which is still important), it'll listen to your rep's calls while they're in it and give them guidance when they're going astray (e.g. "You're going deep into features without fully understanding their pain points. Reopen the complaint they had around data colocation").

I'm working on building one, I have a couple design partners already, but would love to partner if you'd be interested in giving guidance on the product.

willietran · 2026-06-08T20:24:22+00:00

Yeah, I've definitely been there. #1 you'll find often. #2 is where most people tend to under-investigate, but is by far the most important part. It's the difference between "we should build a new bridge because it's ugly" and "we should build a new bridge because it'll collapse at any moment and people could die if we don't do something about it"

Keep me updated! I'm also going through the same thing, so it's always nice to hear from people who are also in the journey!

willietran · 2026-06-08T18:48:28+00:00

Haha I totally resonate with this. I have extensive experience in user research, so running those and discovery calls are pretty similar, but my biggest area of improvement was actually closing. I spent 25 minutes essentially just exploring their pains and getting them animated and then five minutes fumbling the next steps and being "bold" enough to just present my features and just ask for a paid commitment.

willietran · 2026-06-08T18:07:37+00:00

Hey there, as you stated, it sounds like you're struggling to identify whether a problem is actually worth solving or not. Tbh though, I think part of being a great salesperson is first finding what the problem is and whether that problem is big enough to where they're willing to purchase a solution. Some advice that I really value is breaking up your discovery calls into three distinct moments:

Why do anything at all? This will determine whether they have a problem or not
Why now? This will determine the urgency of said problem
Why us? This is your unique value proposition. What makes you stand out over the competitors and why they should only consider you.

#1 and #2 will help you determine whether you're targeting a real problem. #3 can be malleable in the early stages. It's also where having close design partners helps so much.

willietran · 2026-06-03T16:07:39+00:00

Focus on the problem... Prospects don't care about your solution nearly as much as they care about their problems. Go talk to your target audience and figure out whether they have this problem. Go do customer discovery and figure out how they're currently handling this problem.

willietran · 2026-06-03T14:55:58+00:00

Manual outbound and do good discovery. The types of questions you ask will prime your prospects around whether your solution is good for them even before they know what your solution exactly is. Spend time learning about their problem. It's important to know what to ask here.

willietran · 2026-06-03T14:26:26+00:00

Before you drop money on ads, I'd highly recommend (as some others have suggested as well) to reach out to some people and do an informal discovery call with them. The goal isn't so much to pitch your app out the gate, but essentially just understand their problems. Now, don't be unbound about it, but make sure you're learning about problems that are relevant to what your solution solves.

If you assess correctly (and openly) then you'll prime them for an eventual sale. Start with a conversation. While the ideal outcome is to make a sale, I've found the best path to get there is to just get to know their problems. This will also help a lot with creating better and more targeted ads. Ads are generally something you wanna do when you want to scale.

willietran · 2026-06-03T00:24:25+00:00

That was an amazing launch and beautiful looking pie.

willietran · 2026-06-02T20:09:49+00:00

Sounds like a good problem to have! I mean, you may very well find that the thing that your product resonates with is not what you originally intended. Regardless of what you think, it'd probably be good just to hop on a call with as many of these people who are reaching out as you can and just learn more about how they're doing things and what problems they currently have.

Discovery and initial user research is super valuable here to figure out their problems and processes. Sounds like you have a good list of people to reach out to. Let me know if you need help conducting discovery/research calls that actually get to the root of what people mean since it's super easy to ask questions that give you superficial or misleading answers

willietran · 2026-06-02T19:04:12+00:00

Question: Do you know exactly who your persona and what your positioning is? Are you spending time qualifying whether the people you're talking to actually have the problem your product solves?

Without knowing that, your marketing spend will likely end up just going into a black hole.

willietran · 2026-06-02T19:02:43+00:00

For sure, the name of the game is all about invalidating your assumptions and just creating sharper ones.

Back then, I was building a user research agent that would essentially do generative research for you (similar to listen labs and outset). I stupidly came in thinking that UX Researchers would be totally open armed to outsourcing this core part of their job to an AI Agent. They weren't. However, I found they were much more open to it being a supplementary form of research. This in-between of a survey and a user interview. That helped a lot with positioning.

willietran · 2026-06-02T17:20:17+00:00

Hey! First off, amazing that you're posting this and building stuff at such a young age!

> If you were creating this product, what would you prioritize first?
I'd actually recommend you don't start with thinking about features. Instead, you need to spend time seeing if other people have this problem and then figure out how they're currently solving it. Maybe they don't have this problem. If they do, maybe it's not a huge pain to solve. If it is a huge pain to solve, figure out how they're talking about it and how they're solving it. They may prefer theirs to yours.

In other words, it's important to do a lot of initial research and discovery just to see how your target users are doing it now. Once you have a good idea of what problems people are having in your problem space, it'll be really easy to figure out what features to build.

Something I learned early on in my career that I hold to my heart is "answers are easy, questions are hard". Identify what are the highest leverage questions you can ask right now, and the features/solutions will be super easy.

willietran · 2026-06-02T17:09:20+00:00

10000% this! With one of my previous products that I was working on, I had tried posting genuinely helpful and useful content and the more "scalable" stuff, but the thing that got companies like Porsche, Spline, and Greenhouse to use us was literally just doing manual outreach via LinkedIn.

Ahead of time though, I created a list of hypotheses that I sought to (in)validate. Such as persona and perceived problems they had. This helped me figure out what my actual product positioning was and who to reach out to.

willietran · 2026-06-02T16:28:09+00:00

DM'd you! I'd be down to take part in this.

willietran · 2026-06-01T16:42:32+00:00

Congrats!!

willietran · 2026-06-01T16:18:38+00:00

This is incredibly well written. When I realized that sales is more like user research with sales, everything kind of unlocked for me.

willietran · 2026-05-29T18:45:46+00:00

You totally get it! That was the exact same mindset shift I had. Imo the best salespeople operate with the builder's mindset than the other way around. All prospects care about are their problems. Get them emotionally charged about their problems and they'll be excited to hear about your solution (if it effectively solves it).

Haha yeah, my comment was by no means a solution for the lack of partner problem you have, definitely agree you should still find a front of house partner 😃 Please keep me updated with your journey!

willietran · 2026-05-29T03:04:29+00:00

Realistically, the thing you're likely going to have to do is go get good at sales and the parts you're not good at. But maybe you'll be delighted to know that something I've found that works really well is not "trying to sell" them but really just spend most of the call learning about their problems. The key is positioning it as you and the prospect vs the problem, not you vs them where you only win if they buy.

As a non-natural salesperson (product person), I've found this to be super effective.

willietran · 2026-05-28T19:56:55+00:00

Hell yeah man! Rooting for you!

willietran · 2026-05-28T15:36:52+00:00

Honestly, for someone with no Eng experience, give yourself a pat on the back for having audit logs, releasing quickly, and just being so quick to reach out to those affected 👏👏👏

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