Catch up on our Understory Unfiltered episode where Nick Velkovski shares how he bootstrapped HeyReach to $7M+ ARR from Macedonia after Y Combinator rejected him twice.
Nick Velkovski built HeyReach from Macedonia, a country ranked 78th globally for startups with no Stripe, PayPal, or venture ecosystem. After getting rejected twice by Y Combinator, including a rare callback interview, he bootstrapped to $7M+ ARR by treating customer support as his north star metric.
Listen to this episode to learn why Nick credits Y Combinator rejection as company-saving, how the Clay integration created explosive agency adoption, and why his head of support single-handedly rescued the company from tanking.
Nick Velkovski is the co-founder and CEO of HeyReach, a LinkedIn automation platform built specifically for sales teams and lead generation agencies. HeyReach enables scaled LinkedIn outreach through multi-sender sequences and unified inbox management across team accounts.
Nick started his entrepreneurial journey at university in Macedonia, where professors told him startups "don't happen here." He and co-founder Stefan Velkovski built Howitzer, a Reddit DM tool serving NFT projects and OnlyFans creators, before pivoting to LinkedIn automation. Despite Macedonia's limited infrastructure, they've grown HeyReach to significant ARR while maintaining their entire team in their home country.
[00:00] What HeyReach does: Multi-sender LinkedIn automation with unified inbox for agencies and sales teams
[05:30] How Howitzer became HeyReach: The pivot from unlimited Reddit DMs to LinkedIn automation
[08:45] Why Macedonia's startup ecosystem ranked 78th: Building without Stripe, PayPal, or VC infrastructure
[14:20] Nick's mentor became his VP of Engineering: How Marian introduced him to Y Combinator and coding
[18:30] The double Y Combinator rejection: Why getting invited back then rejected again saved the company
[25:15] Two months in San Francisco that changed everything: "Do it for the plot" and IPO-scale thinking
[32:10] How Clay integration created the "holy trio": The partnership that triggered agency adoption
[38:45] Customer support as north star metric: How Ebru rebuilt the department and saved the company
[45:30] The Outbound Sync integration launch: First-ever LinkedIn activity tracking synced to HubSpot
[52:00] "Get rich or die trying": Nick's advice on persistent execution despite societal pressure
Nick and Stefan built Howitzer as a Reddit DM automation tool for their failed startup Beer Money. "We built it as a side project to like a marketing tool for another startup that we had, another startup idea that we failed," Nick explains. Reddit allowed 1,000 DMs per hour at the time, and the tool found unexpected product-market fit with NFT projects, cryptocurrency launches, and OnlyFans creators who couldn't advertise through traditional channels.
The automation expertise they developed on Reddit directly informed their approach to LinkedIn's more complex environment. This demonstrates how successful pivots often come from recognizing that a solution developed for one platform can be adapted to another with different constraints.
Macedonia presents infrastructure challenges that require creative solutions. "Macedonia still doesn't have Stripe, doesn't have PayPal, doesn't have Uber, Bolt," Nick notes. The country's universities were designed to produce outsourcing talent, not entrepreneurs. "All of the universities built their whole programs so they can produce a workforce for this couple of outsourcing companies," he explains.
The cultural resistance was immediate. "I cannot explain to you how much backlash we got. Friends, professors, everyone in Macedonia was like you cannot raise, you cannot push a product. Those things are not happening here." The biggest investment in Macedonia's history at that point was around $100,000. These constraints forced Nick and Stefan to build profitably from day one rather than relying on runway.
The Y Combinator rejection experience fundamentally shaped HeyReach's trajectory. Nick received an interview, got rejected, then received an unprecedented callback two weeks later, the day after hitting $1M in revenue. "I asked around some founders and they said like, this never happened. Y Combinator after they said no, they never reached out to somebody to talk again," Nick recalls.
The second interview happened between two cars in an airport parking lot because it overlapped with their flight. They got rejected again. "From this perspective the guys were right and this thing was much better for us to not raise from them because right now we have all of the freedom," Nick explains. Without VC pressure, they could focus on profitability and customer satisfaction rather than forced hypergrowth.
Two months in San Francisco exposed Nick to systematic differences in entrepreneurial ambition. "In Europe we are dreaming about building a unicorn. In the US the founders are dreaming about pushing the company to the IPO. They don't even mention unicorn," he observes. He also discovered "do it for the plot," the American mindset of pursuing ambitious goals regardless of societal critique.
The experience also revealed European strengths. "We Europeans, we just launch it, we just do it. In my opinion if you combine those two mindsets into one I think you can be unstoppable." Nick now splits his year between the US and Europe, deliberately combining aggressive ambition with execution discipline.
The Clay integration became HeyReach's inflection point. When HeyReach niched down to agencies in late 2023, Clay was simultaneously launching Clay Agent. "Stefan , who is in data partnerships at Clay, reached out to me in May 2024 and was like, 'Hey dude, a lot of agencies are using HeyReach. Let's think about what we can do in terms of native integration,'" Nick recalls.
Agencies began calling Clay, Smart Lead, and HeyReach the "holy trio." As we discuss in the episode, this organic adoption through coordinated GTM engineering workflows demonstrates how native integrations with complementary tools create network effects that accelerate adoption faster than any individual marketing effort.
At traditional SaaS companies, outbound sequences run through sales teams who write their own emails, creating fragmented messaging across touchpoints. As we discuss in the episode, this siloed approach means prospects receive different value propositions depending on which channel reaches them first.
At Understory, we exist to bridge that gap between sales and marketing. LinkedIn outreach through HeyReach becomes an extension of the same messaging strategy driving paid media campaigns, not a separate sales function with its own voice. Sending personalized LinkedIn messages should be considered marketing since it generates demand just like traditional marketing activities. When outbound and paid media share consistent messaging and brand identity, conversion rates improve because prospects receive coherent experiences regardless of touchpoint.
Nick learned this philosophy from Bhub at Smart Lead and Manny Medina, founder of Outreach.io. "It's not just the best product, it's the best product and the best service," Nick explains. This insight came after he completely destroyed their support system in 2024 by having developers handle support duties alongside QA.
The turnaround came when they hired Ebru as a support representative. Within three months, she rebuilt the entire department while handling most tickets alone. "She literally rebuilt the whole department. If we didn't hire her in summer 2024, I think we would have tanked," Nick admits. HeyReach now builds their entire product roadmap from closed-lost reasons and churn feedback, prioritizing features that address why customers leave.
HeyReach's culture eliminates hierarchy in decision-making while maintaining accountability. "We don't have company values like five things that we follow. The whole culture is built by the person coming in really aligning with the team and really acing at the work," Nick explains.
Nick openly admits limitations. "I'm not the best sales guy. I'm not the best marketer guy. I'm not the best designer. But I know how to find the best and I know how to give them a canvas to express themselves." Decision-making happens collaboratively: "Let's sit down, you don't agree with this thing, let's talk until one of us changes opinion and both of us have the same opinion on this topic."
As we discuss in the episode, when doing agency work it's a natural evolution to move into SaaS because you play with so many different products, learn where gaps are, and learn how to plug those holes. This is something Ali and Alex discuss daily at Understory: the patterns we see across client implementations reveal systematic problems that tools haven't solved yet.
Nick's journey from Howitzer to HeyReach exemplifies this. He built automation tools to solve his own marketing problems, discovered unexpected product-market fit, then refined based on real usage patterns. Agency operators have an unfair advantage in identifying SaaS opportunities because they see the same friction points across dozens of implementations rather than just their own use case.
The new Outbound Sync integration allows HeyReach to push live activities directly into HubSpot, launching in beta. As we discuss in the episode, this solves a critical gap: LinkedIn activities previously existed in isolation from CRM systems, making full buyer journey tracking impossible.
The integration shows complete timeline visibility: connection requests, messages, profile views, and subsequent actions like branded search ad clicks and conversions. At Understory, we've seen this granular tracking prove LinkedIn's influence on deals that previously appeared to come from other channels. For agencies running coordinated paid media and outbound campaigns, this integration provides crucial attribution proof that has saved client relationships.
As we discuss in the episode, people misunderstand outbound in three critical ways. First, they only track direct responses instead of an influenced pipeline: 2,000 LinkedIn messages might generate 20 direct replies, but ignore the prospects who visit the website and convert via retargeting. Second, they think about outbound in a silo focused on cost-per-message instead of as a hyper-targeted campaign with personalized messaging. Third, they don't recognize that LinkedIn outbound hits the exact person, not just job titles or demographics, making it more personalized than most ad platforms.
At Understory, we've found that clients who come wanting just GTM engineering or just paid media increasingly ask for the blended allbound approach once they see how the channels compound each other's effectiveness.
Nick's core advice draws from 50 Cent: "Get rich or die trying. Either you're going to be successful or you're just going to die trying to be successful. Those are the two outcomes." Society naturally pushes toward conformity and median outcomes. "Society wants to normalize people to put them into the vast majority," Nick notes.
The key insight involves probability over perfection. "If you try 1,000 things, apparently something's going to work. And you have to be right only once." This mindset sustained Nick through multiple startup failures before HeyReach, and through the Y Combinator rejections that could have derailed less persistent founders.
Want more insight on LinkedIn automation and outbound strategy? Listen to the full episode on YouTube and subscribe to Understory's podcast for more insights on SaaS growth and GTM execution.
Ready to coordinate your LinkedIn outbound with paid media for better attribution? Book a call with Understory to explore how integrated allbound execution can eliminate the coordination overhead of managing separate specialists.
SmartLead founder Vaibhav Namburi shares how 11 failed businesses, WhatsApp community presence, and platform-as-a-service thinking built an email infrastructure managing 5-7 million mailboxes and 110M+ daily warmup emails.
Catch up on our Understory Unfiltered episode where Eli Rubel shares how he scaled MatterMade to $4.2M EBITDA, why VCs are not doing good in the AI era, and how he vibe-coded a SaaS product in seven days.
Hyperbound co-founders Sai and Atul share how 25,000 hand-personalized LinkedIn messages led to accidentally building AI sales roleplay, why reinforcement learning discovers behaviors like "negging mid-market prospects," and their prediction that cold outbound will die within five years.
