Oliver Wind

Building a rocket company by 18.

I’m building Proofioo — helping new freelancers & agencies get their first testimonials and build real proof.

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[Oliver Wind @OliverWind0]

Just realized something critical for my startup:

One of the hardest parts of building a marketplace is the cold start problem.

So for now, I’m the middleman:

Business needs a service → I find the freelancer → make the match.

Do that 10–20 times, then scale.

[Oliver Wind @OliverWind0]

Here is my calendar for tomorrow as a 16-year-old founder. What do you think?

Task:

1. 100+ manual outreaches

2. 7 Shorts + 2 Long-form + thumbnails
• Film

3. Edit as much as possible

I’ll report back tomorrow night to see how much i actually got done.

[Oliver Wind @OliverWind0]

Day 5 of building in public.

Goal: Drop out in 2 months. Move to the US in 6.

Today I did manual outreach (got the first 4 users)

So that's good... but I still didn't even get 1 task fully done out of the 3 I had planned for today (not good enough at all)

[Oliver Wind @OliverWind0]

@Navlio Hey Navlio, thank you so much i'll go ahead and fix them right now : )

[Oliver Wind @OliverWind0]

Hey founders,

Please roast my software product.

I mean… give me feedback.

Be nice though. Please. 😭

https://t.co/XzpameSv7y

Would genuinely love to hear what you think.

[Oliver Wind @OliverWind0]

If you are a NEW freelancer & agency, and you can't get clients because you don't have any proof...

We just shipped the prototype of https://t.co/XzpameSv7y

It's a B2B marketplace that helps freelancers/agency to get their 10-15 testimonials by working for free

So try it out!

[Oliver Wind @OliverWind0]

WE DID IT.

@Proofioo got its first users. 🚀

And not just one…

We got 4.

I know 4 users might not sound like much, but honestly, this is HUGE progress for me.

Still a long way to go, but we’re moving. 🫡

[Oliver Wind @OliverWind0]

@aiml_vis @wojakcodes Yeah, I’d say volume definitely helps, but with 0 portfolio, I’d focus more on getting real work/results first.

Certificates show you’ve learned it, but proof shows you can actually do it.

Have you tried getting any free clients to build that proof yet?

[Oliver Wind @OliverWind0]

@Samuel209691912 @omoalhajaabiola That’s a very valubell skillset 👏 The hardest part now is just getting that first bit of proof.

I’d honestly start by offering a few businesses a free trial in exchange for a testimonial if you get results.

Have you tried reaching out to businesses yet?

[Oliver Wind @OliverWind0]

@LexAutomation Solid start 👏

Here is my advice (not an expert just an outside perspective):

I’d focus on getting testimonials that prove you can actually deliver results, then use that proof to land clients.

What are you doing to build trust with agents?

[Oliver Wind @OliverWind0]

@KachiMarketing1 Nice, how many paid clients have you gotton so far?

[Oliver Wind @OliverWind0]

@Sophy8070amaka Honestly, respect for putting in the work 😭

Personally, i'd focus less on making it perfect and more on showing the real results you can create.

What kind of clients are you mainly trying to attract?

[Oliver Wind @OliverWind0]

@AidanAutomates Hey Aidan, my advice (not an expert, just an outside perspective): get 10 strong case studies that prove your offer works.

But I’m curious—what are you doing right now to build that proof?

[Oliver Wind @OliverWind0]

@NomanNoman40906 Hey Noman, sounds cool. Do you have any client testimonial results so far?

[Oliver Wind @OliverWind0]

@MikeWritesCopy How many clients have you worked by your own?

[Oliver Wind @OliverWind0]

@Ralph4204 @MrCharlesky Nice! I just sent you a DM with something I genuinely think could help you out — figured I could explain it better there.

[Oliver Wind @OliverWind0]

@ashurexbiz Nice, okay! That’s awesome. What kind of results have you generated for your clients? I’m genuinely interested 👀

[Oliver Wind @OliverWind0]

@ashurexbiz I’m no expert, but from sales calls I’ve been on, I usually don’t buy because I haven’t been convinced they can get me the result.

And since I know you’re talented, maybe you just haven’t made that clear enough or what do you think?

[Oliver Wind @OliverWind0]

@ashurexbiz Honestly, that’s a solid approach. Realizing your delivery wasn’t good enough and actually improving it is how you get better.

Can I ask you something real though—do you still get pushback from clients because you don’t have enough social proof?

[Oliver Wind @OliverWind0]

20+ Sales Calls, 0 Clients. Here’s What I Did Wrong, so you don't make the same mistakes.