From failure to $1M ARR in 8
months
After his VC-funded company failed, Jordan Gal turned it into an entirely new product. Eight months later, Rosie hit $1M ARR.
Here's Jordan on how he did it. š
Pivoting from failure
I've been an entrepreneur my entire life. I currently run an AI voice company called Rosie, and we hit $1M ARR within eight months.
The idea for Rosie came out of a pivot. I was running another product called Rally. We raised a seed round and a Series A, but unfortunately, that company just wasn't growing fast enough. We had gotten to a few hundred thousand in ARR and we were closing deals, but it just felt like everything was harder than it should have been.
AI was popping, and I thought to myself, "You know what? We've got a great team, we've got money in the bank, let's pivot and keep going."Ā
Finding the idea
All I knew was that I wanted to get into an AI product. I wanted to build a wrapper because that is where I like to focus in the stack, directly with products that make a difference for the end customer. And I knew I wanted it to be in an AI category that felt very early on and immature.
Eventually, that led me to AI Voice. I remember thinking, "These voice solutions just donāt sound good at all. They arenāt human-like and nobody would want to talk to an agent like this." So I used that natural, negative reaction to the products in the market as my green light. I figured any individual category in AI that was currently bad, was inevitably going to be very good in the near future, and I wanted to start building in that type of a category.Ā
Once I narrowed things down to AI voice, I started digging deeper into the type of solution I wanted to build and the market that I wanted to build it for.
I was coming off the failure of Rally, and a lot of that failure had to do with the market we were selling into. Namely, we were selling to larger ecommerce companies with an enterprise sales process that was long and difficult, with big annual contracts, SLAs, and all of that goes with it. I really did not enjoy it and wanted to go a completely different way with this new product.
That meant building a self-serve, low-friction, low-cost product in the AI voice space. And in my research, I identified SMBs like local service companies and retail businesses as my target audience.
Cutting back but overbuilding
Our priorities when building v1 were speed and overcoming skepticism. That meant identifying a small set of features and overinvesting in the quality of the AI infrastructure we used to build the product.
We trimmed our team down to six people and spent around 90 days getting v1 to a place where we could show something to early users. We sent a bunch of cold emails to meet potential customers and get quick feedback. We then spent another month making improvements and had our first customer roughly 120 days after starting development.
Looking at competitors was helpful, but risky. It helped us identify key features, but we ended up overbuilding. We deliberately set out to build quickly and we still overbuilt!
We made up for it by simply removing features that users ignored over the first few weeks. That turned out to be a good decision. Itās almost a year later and weāve benefited from having a relatively small feature set.
AI stack
Iāve worked with the same cofounder CTO for the last 3 products and theyāve all been Laravel. Weāre fans of the framework and community.
I am not technical myself, but the tech plays a big role in the strategy of an AI wrapper product. So I spent a lot of time evaluating and researching. We ended up partnering with Bland.ai as our infrastructure provider, which has proven to be an important part of our success.
Nothing to lose
Coming out of a pivot from a failed product, a lot of our experience has felt like we donāt have anything to lose. The biggest mistake would have been not pivoting.Ā
Still, we make mistakes constantly. We run a ton of experiments ā price changes, onboarding changes, messaging adjustments, and so on. So we expect to make small mistakes regularly.
Cold emails, ads, and SEO
To get things off the ground, we used cold email to get in front of a bunch of people in our target markets very quickly. It was not efficient, but it brought us our first users and feedback. We worked with a consultant that helped us write the copy, prep the email addresses, and coordinate among a few apps like Mailreef and Clay to send out 1000 emails per day for about 2 months.
Once we had our initial cohort of users, we learned from them, made adjustments to the product, and then started running ads on Meta and Google. That worked well and became our primary source of customers. To be honest, I was really surprised that ads worked for us.Ā
Our relatively quick growth to $1M ARR in eight months came from increasing spend on ads. A key characteristic of advertising as a channel is you can just decide to spend more. You lose efficiency, so you need to monitor and adjust to find the right level, but itās great to have a channel that is so flexible that way.
With ads up and running effectively, I then hired an SEO firm to build out our site and generate external links. I knew that I wanted a more diversified source of customers and my goal was to get to 50-50 between paid and organic channels. And with SEO taking a long time to work properly, it made sense to start investing soon after the ads channel was up and running.
I think go-to-market strategy needs to be matched with your business strategy. If youāve raised VC, like we have, you should be very aggressive as soon as you find a channel that works. If youāre bootstrapped, you need to play it safer and invest only with high conviction.Ā
An advertising fail
A significant challenge we faced was getting absolutely fooled by a google ad campaign.
Thereās a type of campaign called PMax. It allows you to upload a bunch of ad creative (text, video, image, etc) and then it goes out and finds conversions for you through Googleās various ad surfaces. It started working so well on a cost-per-signup basis that we pushed almost all of our budget to it.
I thought we were about to grow like crazy, but it turned out that the signups from this campaign converted at a far lower rate than our other campaigns. It ruined a month of growth, pulled budget from much better campaigns, and worst of all, slammed the brakes on our momentum. We eventually figured it out, but it was very painful.
Make sure you track what happens after signup.
Keeping pricing low
Our approach was to establish a relatively low-priced base tier. We price our base plan at $49/mo and had that as our only option for months. We then opened up higher-priced tiers as we added premium features.Ā
Everyone comes in at the base tier, and we then reveal premium features in the admin where users can decide how far up the value curve they want to go.
And while we offer a low-priced, self-serve product, weāre still a good fit for multi-location businesses. Some of those have turned into much larger contracts.
Finding the right help
When Iām confronting a challenge, I consume X threads, blog posts, and podcasts on the topic. Iāll ask friends about it, ask them for suggestions on who I should talk to, and just dig deeper into the topic. Then, ideally, I can find a consultant to bring into the company to help us work through it.
An example of this is working with Yaakov at Valubyl.com to help redesign our onboarding. I find a lot of value in being able to debate and learn from a specialist. And it really helps our team focus on the project. Nothing like spending money to light a fire under people (myself included).
I see it as my responsibility to go out and find solutions for our biggest priorities. Everyone else at the company is busy doing day to day work and often, the best thing I can do is go out and find the right help for us.
Parting advice
I really hesitate to give too much advice. Thereās no right way to do anything in entrepreneurship. And many of my mistakes were mimetic in nature ā I was trying to do something that was successful for somebody else. That rarely worked out for me.
But here is some advice Iām willing to give:
Whatever you think you need to start, you need less. Donāt give yourself excuses that get in the way of getting started.
Be more ambitious. The market is unbelievably big. It rewards ambition.
Ignore vanity metrics like money raised and partnerships and even revenue ā what matters is after-tax money in your personal bank account.Ā
What's next?
My goal with Rosie is to become the Mailchimp of AI voice. What I mean by that is for Rosie to be an entry point for many thousands of small businesses to use AI to answer their phone.
The way we can do that is to build a great product that is easy to use, and to get word of mouth through great support and satisfied customers.
You can follow along on X and our Offsite podcast. And check out Rosie!
Leave a Comment
A great struggling and inspiring story of AI startup
Incredible turnaround, Jordan ā Rosieās journey proves what I see with SaaS founders every week: failure is data, not defeat.
Your pivot highlights the essentials:
Nail Product-Market Fit by solving one urgent problem for a clear ICP
Run agile Go-to-Market tests and double down only on traction channels
Keep pricing simple and execution fast
This is the exact playbook I coach founders through to reach $1M ARR without burning 18 months of runway. Truly inspiring.
š I help SaaS founders apply these frameworks ā happy to connect with anyone on a similar journey.
Amazing tips. Very inspiring, thanks for sharing.
Here for this. š
As almost a decade long founder/programmer a few things in this hit home:
Opinionated v1 with a tiny team (90 days) ā then delete what users ignore. Most of us try to pre-optimize; your ācut after launchā stance is a great reminder.
Self-serve SMB focus instead of enterprise contracts. That switch alone explains so much of the speed.
Ads as the throttle, SEO as the base, and the hard-won lesson on PMax (optimize for activated users, not signups). Been burned there too.
Curious on a few specifics if youāre open to sharing:
Activation metric ā what single action best predicted paid retention (first successful call? N calls? an integration?)
Ads ā which creative/message actually moved the needle (problem-pain vs. āAI receptionistā benefit vs. pricing)? Any CAC payback guardrails you used while scaling?
Overbuild ā trim ā whatās one feature you were sure you needed but usage proved otherwise?
Onboarding ā for non-technical SMBs, what solved the āfirst success in 60ā90 secondsā moment?
Huge respect for turning a tough pivot into momentum. This is the most practical $1M-in-8-months breakdown Iāve read in a while.
Arenāt you afraid of being sherlocked by RingCentral or OpenPhone (both of which have AI receptionists as a feature)? Same goes for FSMs like Jobber that offer a more autonomous voice assistants that go beyond just answering phones (think outbound follow ups, tasks, etc.) Certainly something to think about as this space heats up!
Loved this read! The parting advice is perfect is so so true. š
All the best...!
good one <3
Great story, like it very mutch
Very nice story.
hello Jordan, Wow, what a motivating story! When others would have given up, you turned a failure into a success. It's very inspiring. Thank you for sharing it with us.
Really inspired by Rosieās mission, building something that goes beyond just a product and creates real community value. What stands out to me is how important it is to understand the signals behind what keeps users engaged and coming back. Excited to see Rosie grow, and Iād love to keep learning from the way youāre shaping this journey
Curiousāwhen you say you āoverbuiltā features early on, was there anything that surprised you when you saw how users reacted? And did any specific channel outperform others as you scaled to $1M ARR?
That's a powerful story of resilience and strategic thinking. Thanks for sharing!
This is such a great breakdown of how you turned a tough pivot into a huge win. I really like how you used your own frustration with bad AI voice products as a signal that there was a big opportunity there. Focusing on SMBs and making Rosie low-friction/self-serve seems like a smart move compared to long enterprise cycles, and hitting $1M ARR in eight months proves it worked. Love the honesty about overbuilding too ā itās a great reminder that cutting features based on user feedback is just as important as shipping fast.
Where are how were you sourcing your contact lists for your email campaigns? Or was the consultant providing that?
Huge inspiration. How do you find Bland? I've also been experimenting with it and it's insane.
Hitting $1M ARR in just eight months after a pivot is absolutely wild! š Super inspiring. To stay motivated to dive into a completely new product after Rally didnāt work out is really hard. Thanks for sharing such a raw journey!
Great readāthanks for sharing. Weāre building EcoAppraise, an AI tool to cut through PR noise in the environmental space and help people distinguish real impact from greenwashing. It rates claims/stories/projects with a simple credibility score.
Since you referenced advertising: which channels actually worked for you (search, social, newsletters?), roughly what did you spend early on, and what ROI/ROAS did you see? Our niche is narrower, so benchmarks would be super helpful.
It sounds like you were able to spend some of your remaining VC "money in the bank" on the pivot. Were your investors a part of the pivot planning or did you have the freedom to switch it up (especially if everyone already agreed the originally-funded idea wasn't working out)? I'd have hated to be trying to pivot while also trying to keep the original business afloat just for the sake of my investors' expectations.
super stuff
Thanks for your story it was really inspiring
This is awesome,
love how you turned a setback into a rocket launch. The focus on overbuilding quality, learning fast, and keeping pricing low really shows why Rosie hit $1M ARR so quickly. Inspiring stuff!
Also curious, wondering if something like Startup Solve, which helps founders validate and grow AI startups, could gain traction just by smart positioning like this, without traditional marketing?
āTotally feel this ā losing track of convos or tasks kills momentum. Iāve been working on an AI memory engine (Elcan) that tackles exactly this. Curious, whatās your biggest challenge with keeping track of tasks from email/Slack/etc?ā
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Love this breakdown. What stood out to me is how you reframed the āfailureā into momentum instead of letting it stall you out. Iāve noticed a similar pattern in early projects Iāve worked on, the pivot usually looks obvious in hindsight, but at the time itās messy and scary. Curious: was there a single metric or signal that gave you the conviction to double down after relaunching, or was it more of a gut call?
"Whatever you think you need to start, you need less. Donāt give yourself excuses that get in the way of getting started."
Truer words. They call it "boot strapped" for a reason.
Congratulations on your pivot, vision, hustle, and ability to work with "enough".
Wild turnaround, Jordan, going from a miss to $1M ARR in 8 months shows ruthless focus.
Big takeaways for me:
Narrow problem ā opinionated v1
Fast feedback loops with real users
Distribution matched perfectly to buyerās moment of need
Curious on two fronts:
Which single channel actually moved the needle (not just correlation)?
What activation event best predicted upgrades ā first successful run, certain # of uses, or something else?
If you had to repeat this sprint, what would you deliberately skip?
P.S. Iām with Buzz , we design conversion-focused Webflow sites and SEO for product launches. Happy to share a 10-point GTM checklist if useful.
Not the first PMax horror story I've heard!
Thanks for sharing your experience and pivots!
Hey everyone,
Iām Musa, 20, based in Nigeria š³š¬. Iām building Elcan ā an AI Memory Engine for Work.
It connects to your email + work tools and turns every conversation, task, or decision into permanent, searchable memory.
It also extracts tasks automatically and creates smart follow-ups, so nothing slips through the cracks.
Iām super excited to share my journey here, connect with other builders, and get feedback.
If youāre curious to test Elcan, hereās the waitlist:
Thatās an incredible turnaround. Curious to know, what was the biggest mindset or strategic shift that helped you go from failure to $1M ARR so quickly?
Really inspiring turnaround, Jordan, the speed and focus are impressive.
Iām in the opposite lane right now, bootstrapping solo. Been building Coupyn, a community-driven coupon/referral code platform (100k+ companies listed). Nowhere near $1M ARR yet, but reading stories like this is fuel to keep going.
Curious, looking back, was there one key distribution channel that gave you confidence early, before ads started scaling?
What a turnaround, Jordan! From Rally to Rosie at $1M ARR in 8 months, Read your entire journey each by line , thats a serious execution.
Love how you kept it lean with cold outreach, ads, then layered the SEO my friend.
At GudSho, we see many brands scale the same way, with video adding that extra lift early on.
Wishing Rosie all the best man - It would be great to see how video fits into your next growth chapter! If possible give it a try with GudSho. I think it will resonate with you and your audience.
Thanks mate.. all the best.
Such an inspiring story! Turning a setback into $1M ARR in just 8 months shows the power of persistence and focus. Really motivating read.
wow
informative
Thatās an incredible turnaround, a big respect. Iām curious, was there a single decision or shift in strategy that unlocked the growth curve? Or was it more about compounding small wins consistently?
Great story, it really inspired me. Thanks for that!
what a story, keep going bro!
Really inspiring journey, Jordan!
Really appreciate you sharing this. It was super helpful and I learned a lot.
Loved this writeup, Jordan. Cutting features after launch instead of before is such a solid move. Do you think growth came more from timing with AI voice or from keeping the GTM simple?
What I like about this story is how Jordan didnāt treat failure as the end. The real trap is sticking with something that isnāt working just because youāve already invested in it.
He pivoted with momentum, kept his team, moved fast, and had paying customers in months.
Big takeaway: freedom comes from cashflow and leverage. Build something simple, scale it with systems, and use the cashflow to buy assets that keep paying you.
Who here has ever walked away from something āworkingā to chase something better?
Great no-BS build story. Fast, scrappy, sharp and you didnāt bloat the team either.
So many early-stage startups trip over hiring and HR stuff without realizing it. I work with founders to clean that up before it turns into an expensive oops.
i think my experience bootstrapping saas startups previously was very helpful. i just went back to that mindset and ignored that we had raised VC.
This user demand surprised me. It is another classic case of AI successfully transforming into valuable products. This is impossible without AI.
surprised me too!
Wild Success Story good work
thank you!
āWild turnaround. When you pivoted, did you already have a sense AI was the right move, or was it trial-and-error until something stuck?ā
the thing that really drew me toward AI was the demand from actual customers. i was worried that a lot of the demand we all see on twitter comes from developers for dev tools, which we weren't involved in. but i have a few friends that were selling AI tools to non-devs and i wanted that same level of demand from customers.
Low-key this should be required reading for anyone building AI wrappers. Itās not about some genius prompt, itās speed, channel testing, and just giving a damn about what works.
hell yeah. i'm not technical. all i care about is customer demand.
Super inspiring! Love how authentic this feels.
just trying to be honest as much as possible!
Inspiring story indeed, I like the fact that you perfectly stated your shortcomings and improved on it.
always plenty of shortcomings :)
Informative, Indeed a new lesson
This post is so authentically written that it doesnāt seem to be from a successful entrepreneur, but rather from an everyday hustler in the neighborhood.
just talkin facts without the bullshit!
haha you can even talk street too
This post is so authentically written that it doesnāt seem to be from a successful entrepreneur, but rather from an everyday hustler in the neighborhood.
Inspiring! As I want to build an AI-driven product, it's a new lesson for me!
I am already working on my own project with 0 knowledge ai do help a lot
Thatās an amazing journey ā going from failure to $1M ARR in just 8 months is truly inspiring. It really shows how the right strategy and consistency can change everything. For anyone looking to learn practical steps, hereās a helpful worth checking out.
Huge congrats ā and thanks for sharing the low points too. A few concrete Qs that would help other makers learn from this:
1) Finding PMF after failure
ā¢ What changed post-failure: the wedge, ICP, or the core job-to-be-done?
ā¢ What was the first metric that told you āthis time itās workingā (activation, D1/D7 retention, pay-conversion)?
2) Distribution
ā¢ Which channel actually moved the needle (cold outbound, content, integrations, marketplaces, communities)?
ā¢ Any ānon-obviousā loop you discovered (e.g., product embeds, referrals, partner co-selling)?
3) Onboarding ā activation
ā¢ What single action correlated most with retention/revenue? (e.g., connect data, invite a teammate, ship first task)
ā¢ Did you run a 60-sec āfirst successā and measure first_success ā paid?
4) Pricing & packaging
ā¢ Did ARPU come from seat-based, usage, or value-tiered pricing?
ā¢ What was your first meaningful paywall and why did you choose it?
5) Sales & ops
ā¢ Rough CAC payback and deal velocity (self-serve vs light sales-assist)?
ā¢ Team shape while scaling from $0 ā $1M ARR (eng/product/gtm headcount)?
If youāre willing to share a rough reverse-timeline (Month -8 ā Month 0 with 3ā4 milestones), thatād be gold. Thanks again for the candor!
Wow sounds amazing! I love how many helpful AI solutions are coming
my goal was bringing AI solutions to completely non-technical customers.
I especially like the advice and of course the whole story! And I would like to hear more when you targeted the product Mailchimp as the goal, tho I think ai voice still has long way to go, at least now I can't find any platform is very good for using
when it comes to the mailchimp analogy, i didn't want to go too hard at one vertical. i wanted to build an entry-point platform for millions of businesses. that meant building something really easy to onboard and giving up some of the depth of a very verticalized product. like mailchimp!
Love the pivot mindset ā especially turning ābadā AI categories into opportunities. Super inspiring as Iām also building AI tools to automate business operations.
Wow that is amazing. Wish I would build something too
āThanks for sharing this, James! Really inspiring story. If you had to point to one decision that made the biggest difference in reaching $1M ARR, what would it be?ā
getting ads to work and then being willing to spend a lot on the ads tbh
A truly amazing story
š
Really inspiring journey, Jordan! I love how you turned a failed venture into Rosie and hit $1M ARR so quickly. Your point about experimenting with different channels and then leaning into what works resonates a lot. I run an agency helping SaaS companies set up analytics, run ads, and turn visitors into paying customers. Your point about tracking āpaying customersā versus just āsignupsā on those ad platforms really hits home.
oh man we really screwed this up a few times by being focused on the wrong thing. needed to completely focus on campaigns that brought in activated users. just going after "signups" without looking further into the funnel cost us big time.
Yeah, no surprise ;)
watching rosie hit $1M ARR in 8 months really blew me away the focus and speed are impressive, and it shows that in startups you have to be bold and willing to pivot.
amen gotta play to WIN!
Great SaaS, entrepreneur journey, it feels a very good approach for any SaaS start up launch. I will look at using similar plan that yours for my startup App called DataInsightAI. Good luck in your venture, I wish you all the best.
Honestly, your journey really resonates. In startups, failure isnāt the end itās one of the best teachers. I love how you werenāt afraid to pivot, kept things simple, and just kept moving forward. The way you nailed both product and marketing is super inspiring!
Well written. Lessons well documented. Thanks a lot.
appreciate it!
Well done, i also want to build an AI product i am dont know where , how to start , as i am not aware tech related things , you built this product gives me good motivation.
Honestly, your journey really hits home! In startups, failure isnāt the end itās actually the best teacher. Love how you guys werenāt afraid to pivot, kept things simple, and kept pushing forward. The way you nailed both product and marketing gave me a ton of inspiration!
your story shows the power of pivot + focus:
1ļøā£ Pivot fast when traction stalls
2ļøā£ Go lean ā 6-person team, 90-day v1
3ļøā£ Start with cold email ā scale with ads + SEO
4ļøā£ Keep pricing simple ($49 entry) ā expand up the value curve
5ļøā£ Remove ignored features ā double down on what users love
Hitting $1M ARR in 8 months wasnāt luck ā it was clarity, speed, and smart GTM.
#SaaSScaling #ProductMarketFit #ARRGrowth #GoToMarket #SaaSCoaching
the story shows that resilience, smart pivots, and relentless focus can turn things around faster than most people imagine. Itās an inspiring, no-fluff example of how determination combined with the right strategy leads to explosive growth.
How did you figure out the specific copy and visuals that converts in your ads? It's awesome when you can get ads to scale like that but I'm guessing it took some experimentation up front to figure out what actually worked
Really helpful ā weāre experimenting with repurposing prompts into productised templates. Small wins: faster content for beta users and clearer value proposition.
Thank you! Lot of factors, including luck and having cash in the bank to spend all helped.
Really enjoyed this story...... especially how you leaned into AI voice when most products in the space still sounded terrible. That āif itās bad now, itāll be great soonā mindset is gold.
Wondering ..... as Rosie scales, do you see it becoming more like a 24/7 receptionist that can handle full conversations, or will you keep it focused on short, high-accuracy call handling for SMBs?
Thank you! I see the base plan as an answering service, and the higher tiers as a receptionist that takes more human-like actions.
Weāll add more functionality and integrations, but slowly.
All the best :)
Incredible turnaround! Love how you spotted the right moment to pivot and went all-in. Super inspiring for those of us still early in the journey.
I legit had to ignore the emotional side of things. If I thought about it too much Iād hesitate. So once I got excited about it I just went. And very importantly, had a tight group of people who loved working together who wanted to keep going.
What pushed you to keep going?
Same thing as always. The prospect of making millions of dollars for my family!
i think you can have an affiliate link perhaps to help you.
We have an affiliate program for anyone that wants to promote Rosie. Itās in the footer on our site. (I think thatās what you meant!)
woļ¼is so coolļ¼
Have you changed your mind about your audience since starting?
Proof that failure isnāt the endāitās just the plot twist before the breakthrough. š From rock bottom to $1M ARR in 8 months? Thatās grit, strategy, and a little bit of magic
Hell yeah šŖ
So helpful to know about Mailreef and Clay; didn't know about those so will give them ago. I really appreciate this honest, candid view of what worked and didn't work.
Appreciate the feedback!
Mailreef in particular is awesome. Great service and great people. And they have a done-for-you option we are using now.
Awesome thanks, Mailreef here I come!
Do you have an affiliate link perhaps?
No but tell Mike I sent you!
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