Ask HN: What weird or scrappy things did you do to get your first users?

13 points by preston-kwei 150 days ago | 10 comments

Hi everyone,

I’m building Persona, a platform to delegate email scheduling to AI. Lately, I’ve been working hard to get those first users on board, but it’s been quite challenging.

I’ve already tried the typical strategies that everybody talks about: cold email, LinkedIn InMail, careful targeting, decent copy. It’s mostly been a dead end. Low open rates, almost no replies.

At this point, I’m not looking for the usual advice you see in blog posts or on reddit. I’m specifically curious about unconventional or non-obvious things that actually worked for you early on, especially things that felt a bit scrappy, weird, or counterintuitive at the time.

If you’ve been through this phase, what genuinely worked and got you your first users?

lightyoruichi 149 days ago |

Hi Preston, I took a look at this and here's my comments:

  - Wrong ICP, "early stage founders" is not a buyer. They don't have enough email spam problems. Later-stage founders who do already have an EA.

  - You're assuming the pain. People generally don't have problem with email scheduling. And if someone were truly spending 6+ hours a week on it, they would have already delegated.

  - The messaging framing hurts you. The moment Persona is compared to a human EA, you lose on judgment, context, and trust.

What could work though,

  - Narrow to a pathological edge case. One role, one moment, one acute pain.

Examples: solo VCs without EAs, boutique bankers mid-deal, lawyers coordinating multi-party calls under time pressure, founders actively fundraising without support.

  - Reframe away from scheduling. Don’t sell logistics or efficiency. Sell control. This is a way more powerful messaging instead.

  - Stop outbound. Insert parasitically into their workflow. Live where the pain already exists. Gmail plugins, CRM edges, investor update workflows. Be an appendage, not a destination.

  - Accept that this may not be a standalone company. It may only survive as a feature inside a larger assistant or email client.

I know it's a bitter fruit but think about this and digest it. This isn’t about tactics. The problem doesn’t hurt enough for the people you’re targeting, at the moment you’re targeting them.

preston-kwei 147 days ago | |

Thank you for your response. I think the ICP needs some refinement. I've found it pretty hard to prospect because it is so broad.

> People generally don't have problem with email scheduling I think this stems from the fact that there is no existing tool that solves this problem. Clearly, tools like Calendly haven't solved it for execs or people with complex scheduling flows. A lot of it is caused by the fact that people tend to just tolerate scheduling because they don't know a better way, leading them to waste more time than they expect.

> The moment Persona is compared to a human EA, you lose on judgment, context, and trust. I agree with this. I'm trying to steer away from this actually, because a lot of companies sell an AI EA, even though their product doesn't even do anything related to EA tasks.

I think the landing page needs more work, copy wise. I'm certainly moving towards the control thing. The features are in place, so I need to tweak our marketing.

> Accept that this may not be a standalone company Totally. Scheduling alone cannot be a standalone company. That's just the first pain point I'm attacking. I have many more features that are in progress that move it more into it's own category. Think of it more as a email delegation layer for AI agents.

Thanks again for your thoughtful response.

superdisk 150 days ago |

I worked on a language learning site and in order to try to onboard tutors, I wrote a script that scraped the Preply tutor list, which gave first names, pictures, and a YouTube account link.

From there I made a spreadsheet and spent hours googling names and trying to match up pictures to faces, sending messages asking if they'd like to be a part of a pilot program on my platform.

Got quite a few people willing to try it out :) but sadly the startup didn't succeed. Fun times though.

preston-kwei 150 days ago | |

Interesting! I bet now with AI, you can create an agent to do this. I'm glad that worked, however, we're targeting founders of b2b saas companies who are early stage, and that is quite a broad search.

Grisu_FTP 150 days ago | | |

if someone annoyed me with ai like this, i wouldnt even waste the energy on an AI summary.

On the other hand, im probably not good enough at anything to even be worth the waste of energy to annoy me.

Soerensen 147 days ago |

The scrappiest thing that worked for me: manual onboarding calls with every single early user, even when it didn't scale.

I'd hop on 15-minute calls to understand their workflow, then send them personalized Loom videos showing exactly how to use the product for their specific use case. Time-consuming? Absolutely. But those users became evangelists because they felt ownership over the product direction.

A few other things that moved the needle early:

1. Commenting on niche subreddits where your target users actually hang out - not to pitch, but to genuinely help. When people see you're knowledgeable, they check your profile. Make sure it mentions what you're building.

2. Finding "trapped" users on competitor platforms. Look for complaint threads about existing tools, then reach out directly with "Hey, saw your frustration with X. Would love to show you how we solve that specific problem."

3. Making your first 10 users feel like co-founders. Give them direct access to you via text/Slack. Ask their opinion on features. They'll fight for your product's success.

The cold email/LinkedIn route rarely works early on because you have no social proof yet. Much better to go where conversations are already happening and demonstrate expertise first.

PretzelJudge 150 days ago |

I like this quote:

> First time founders are obsessed with product. Second time founders are obsessed with distribution.

I have personally grown an app from zero to 100k+ users, with no marketing budget. I don't have a magic formula, but i can say in hindsight that the first 5 users were harder to get than the next 999,995.

Here was my secret: I begged. Finding 5 people to actually use my product was soooo freakin hard. Once I got to ~100, organic growth started to take over, but things like responding to emails, fixing bugs and looking into new features right away make early users personally like you and more likely to tell their friends.

The hard part is finding the right people at the right time. I googled "Persona email scheduling" and found https://usepersona.app/, so I'll assume that is you. I don't know much about your product, but i assume you are targeting people who need to schedule lots of meetings. I have a few notes:

1) Your pricing is crazy. $660/year is a lot for automated meeting scheduling. Your comp should be Calendly which is closer to $10/month.

2) What problem are you trying to solve? Calendly seems pretty close to the perfect solution for one-on-one meetings. This seems to be for scheduling larger groups. Make that clear at the top of the page. If you are directly competing with Calendly, then just make that clear.

3) I'm not the audience, but think about who really has this problem. For me, 90% of my group meetings are scheduled within my company and we use Google calendar to find times that work. I dont do this enough that I'd feel compelled to try out a new product. Sales people schedule lots of 1-on-1 calls, but not sure that group calls is a big issue. So think about who this is really for. In general, just about the only time i will try a new product is if it provokes my curiosity (not gonna happen for a meeting scheduling bot) or it is solving a problem I need solved right now. Some products are really great, but finding the right person at the right time is a huge challenge. This is why I brought up the quote at the beginning. The right product with no distribution is very hard to get off the ground. I'd say that your early goal should be to find power users if possible... if you try to spread too wide of a net, you will probably fail. Better to have a few people who love your app than a larger group of people who think it's nice.

4) Let's say you do get a few users. Well, you are an email scheduling tool, so distribution is actually built on. On your free or basic plans, you can have a banner at the bottom of outgoing emails that says "This email was drafted by Persona, the tool for automated emails". Now you have free marketing on every email that goes out. Same way that my calendly link is free marketing for calendly. If people want that banner removed, they can upgrade their plan.

Again, take this advice for what it's worth, which is very little, since 1) I dont know your market well, and 2) what worked for me may not work for you.

Jeetu456 149 days ago |

I went through the same funnel, but no response

- Wrong ICP, "early stage founders" is not a buyer. They don't have enough email spam problems. Later-stage founders who do already have an EA. - You're assuming the pain. People generally don't have problem with email scheduling. And if someone were truly spending 6+ hours a week on it, they would have already delegated. - The messaging framing hurts you. The moment Persona is compared to a human EA, you lose on judgment, context, and trust.

- Reframe away from scheduling. Don’t sell logistics or efficiency. Sell control. This is a way more powerful messaging instead. - Stop outbound. Insert parasitically into their workflow. Live where the pain already exists. Gmail plugins, CRM edges, investor update workflows. Be an appendage, not a destination. - Accept that this may not be a standalone company. It may only survive as a feature inside a larger assistant or email client.