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?
- 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.
- Narrow to a pathological edge case. One role, one moment, one acute pain.
- 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.
> 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.
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.
On the other hand, im probably not good enough at anything to even be worth the waste of energy to annoy me.
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.
> 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.
I've found myself procrastinating a lot when it comes to trying to acquire users. It's a lot more fun to build features than it is to do cold outreach. Yes, you found the site :).
1) Understandable, let me reply to the other 3 points to see if pricing makes sense after that.
2) We’re not trying to replace Calendly. Calendly is great for link-based 1:1 scheduling, but many execs still operate primarily over email and actively avoid sending links. Persona is an email delegation layer that handles inbound scheduling end-to-end: proactive follow-ups, coordinating across long threads, and dynamically rescheduling when higher-priority contacts come in. That distinction should definitely be clearer on the landing page.
3) Fair point that you’re not the audience. We’re focused on founders and execs who spend a meaningful amount of time coordinating meetings over email. For them, the pain isn’t finding a time once, it’s the constant back-and-forth, follow-ups, and reshuffling priorities. Not everyone can afford a human EA, and link-based scheduling tools can’t handle that level of personalization (talking to an investor is very different than a friend). Research we’ve seen shows execs still spend 6+ hours per week on scheduling.
4) That’s a good point, and we’re thinking along similar lines. Since Persona operates directly over email, there’s a natural distribution loop there, similar to Calendly links, and we plan to lean into that more deliberately. Would you be bothered if you were on our 23/mo plan and still had a banner there? Also, do you think there should be a free tier beyond the 14 day trial?
Thanks again for taking the time to respond.
Software for teachers. Teachers tend to talk to each other, which is great for distribution. On the other hand, they have very little spending power. But back on the other hand again, they don't get as many cold emails as execs do.
> Research we’ve seen shows execs still spend 6+ hours per week on scheduling.
Be very careful not to delude yourself here. No one is spending 6+ hours a week on scheduling who is willing to use your tool. That's almost a full workday. If you are at this point, you probably have a human assistant who handles this.
> Would you be bothered if you were on our 23/mo plan and still had a banner there?
Probably not. But if i were, i'd probably just upgrade to a higher plan.