Adam S.

My life thesis: execution > strategy. Compounding FTW. I'm an optimistic skeptic. Curiosity is the most important quality in life.

I enjoy pattern matching and read widely. The opportunity to learn every day is a gift. Time is precious. The ability to improve what and where I focus and delegate the rest is ideal. 

I [of course] love my family and friends. I believe I am a logical, thoughtful adult and therefore accept my choices. I am content and therefore I have won.

Founder and CEO @Chore. We are a founder's back-office (HR, finance, compliance, equity) operations team. Back-office operations are an undifferentiated tax on success. Focusing on your superpower enables success. Chore handles the rest (i.e. we specialize in ops so you never have to) so you can achieve your dreams. 

Host of the Entrepreneurial Excellence podcast. I dive deep with multi time founders about their key decisions, actions, hires, drivers and more that they use to achieve "excellence." 

General Partner at the Autopilot Fund. We invest in early stage startups. We love obsessed founders who have a history of breaking through walls. I have invested in over 200 startups across multiple funds. 14 are unicorns (8 from seed).

In previous lives, I founded 3 other companies, been a product leader on a big co API team, Chief Revenue Officer (CRO), Chief Operating Officer (COO), and do-it-all janitor. 

I enjoy building great teams, processes, and stories that unify a company around a shared mission. Helping others build successful businesses brings me joy. More successful startups = a better, more dynamic world.

People describe me as energetic, positive, creative, detailed and optimistic. I enjoy rational, logical, data driven debate built on mutual trust and respect. I'm not an engineer but people view me as "technical" and have built companies with the brightest PhDs and brilliant engineers. The best compliment I received was "you ask great questions."

Honesty, trust, fun, a sense of urgency and mission are what I look for in colleagues and places I work. Passion about my product, my company and my team is what drives me. I work hard and enjoy being surrounded by people who do the same. 

"Leave the world (and your business) better than when you arrived..."
"The greatest risk is not taking one!"

Always curious and learning. Subscribe to Entrepreneurial Excellence to learn.

General Partner

The Autopilot Fund focuses on early-stage companies that serve and accelerate how companies operate. 

More about us: https://autopilot.fund/

Operations span various “departments”: could be in engineering, operations, sales, finance, product, customer success… the questions we ask ourselves are:

1. Is this a founding team so capable that others should be afraid to go against them?
2. Do they understand the problem better than anyone, and have special “founder-market” fit?
3. Will they rest until they have dragged the world kicking & screaming into their vision of the future?
4. Is the product “infrastructure” in a manner of speaking: structured data, deeply embedded, sticky?
5. Does the advent of AI exponentially increase or decrease their defensibility?

Our portfolio includes some pretty special companies like AngelList, Pulley, Puzzle, Levels, Disco, among others. 

Smart founders focus. Bad founders distract themselves with all the small, non-product, non-customer work that can easily take up hours but not move your startup forward.

We are sector agnostic and focus mostly on early stage. Our thesis is simple: the best founders come from anywhere, with any background, working in any industry. Focus, joy, dogged determination, and deep knowledge about your product and how you're changing the world is what leads to success.

If you're interested in learning more, drop me a note on LinkedIn.

Premesh Purayil is a seasoned technology executive with over two decades of experience leading innovation at the intersection of advertising, data, and digital transformation. As Chief Technology Officer at OUTFRONT Media, he is driving the modernization of the out-of-home industry by expanding digital out-of-home (DOOH) and programmatic capabilities to deliver measurable, data-driven results for advertisers and publishers.
At OUTFRONT, Premesh oversees a unified technology and product organization focused on operational excellence, automation, and yield optimization. Under his leadership, the company is redefining how technology powers creativity, audience targeting, and campaign measurement across digital and physical media. His mission is to align business and engineering strategies that create scalable value and position OUTFRONT at the forefront of AdTech innovation.
Prior to joining OUTFRONT Media, Premesh served as Chief Technology Officer at Freestar, where he led global product and engineering teams through a period of rapid growth. He spearheaded multiple video and header bidding solutions, advanced SSP/DSP integrations, and established Freestar as a leader in publisher monetization. Earlier in his career, he was the CTO at Ranker, where he built the engineering organization from the ground up and developed proprietary ad solutions that significantly increased revenue and engagement.
Throughout his career, Premesh has been recognized for his deep technical expertise, collaborative leadership style, and ability to translate complex technology into business outcomes. He has contributed to industry thought leadership through conference presentations and articles on the evolution of AdTech, programmatic trading, and the future of DOOH.
Beyond his professional achievements, Premesh is passionate about building diverse, high-performing teams and fostering cultures of innovation. He actively mentors emerging technology leaders and believes that curiosity, transparency, and disciplined execution are the cornerstones of sustainable growth.
Premesh holds a strong belief that technology should not only enable smarter advertising but also elevate the broader media ecosystem by connecting creativity, data, and insight in ways that drive real impact.

Premesh Purayil

I keep seeing the same misconception around AI, and I think it's what's causing pilots to stumble.

Ever since artificial intelligence came on the scene, we've been talking about it like it's the solution to all our problems. Plug it in, and let the magic happen, right?

But this fundamentally misunderstands one thing: AI is not a strategy. AI is a tool that amplifies your strategy (whether it's good or bad). Try to plug AI into a bunch of unoptimized, siloed workflows, and you'll still have an unoptimized, siloed organization.

Instead of starting with AI, start with solid strategy. Then bring automation in.

Chief Technology Officer, OUTFRONT Media | AdTech & DOOH Innovator | Driving the Future of Data, Measurement & Media Transformation

The open web isn’t “dying”, but the economic model that sustained it already has.

As AI becomes the primary interface to information, we’re quietly breaking the bargain that funded independent publishing: discovery → visits → sustainability.

This piece isn’t about nostalgia for the old web. It’s about second-order consequences, especially what happens to AI itself when the incentives to create original knowledge collapse.

Curious where this leads, and what survives.

This isn’t a hot take. It’s a conclusion drawn from watching the same structural pattern repeat faster each year, with fewer escape hatches. The open 

Open article: The Open Web Is Dead. What Comes Next Is a Problem for AI by Premesh Purayil • 5 min read

The Open Web Is Dead. What Comes Next Is a Problem for AI

Thank you, Greg Wise, for this. I get asked the same question all the time, and the honest answer usually starts with: “it depends.”

One important reality: buying one billboard spot is often not enough unless you’re a local retail business using it for the “turn left here” moment, which is still incredibly valuable.

Like online media, OOH works best when you think in terms of journeys and frequency. Multiple placements along your target audience’s real-world path create reinforcement that digital alone can’t replicate. Trust in the real world is earned and repeated physical presence plays a big role in that.

In fact, I just heard a great example: someone was in a taxi, saw an ad on their phone, then saw the same campaign on the in-cab screen, and then again on a billboard as they got out. That’s true omnichannel execution and we should be doing a lot more of it.

#OOH #IRL #OUTFRONT

Co-Founder & Chief Customer Officer at OneScreen.AI | Co-Host of the Beyond The Billboard Podcast | Ex-HubSpot

“How much does a billboard actually cost?”
 I get this question weekly. So let’s make it real and use Chicago as an example 👇

If you’re thinking about OOH in Chicago, here’s the rough range of what brands actually pay per month:

Downtown wallscape (Loop / River North, big hero units)
 → $30K – $60K / month
High impact. Big creative. Great for launches, funding announcements, and “we’re legit now” moments.

Dan Ryan Expressway — right-hand read (prime commuter flow)
 → $15K – $30K / month
This is classic, high-frequency, everyone-sees-it inventory. Amazing for sustained presence and brand building.

 I-55 — further from city center
 → $3K – $6K / month
 Still strong reach, but less density + less prestige. Great for stretching budget and adding frequency.

A few important caveats because OOH is not a menu with fixed prices and quite frankly, pricing can feel a bit all over the place:
 • Everything is estimated until it's not
 • Availability matters (scarcity is real in Tier 1 markets)
 • Negotiation, relationships, technology + packaging can swing pricing a LOT
 • Long-term or multi-market deals = better economics

The right board in the right place for the right objective will outperform a random “good deal” every time.

And this is why I always tell brands:
Don’t wait until you “need” OOH.

 Start thinking about markets, moments, and budgets before the launch / fundraise / big push.

I think 2026 is the year we're really going to lean into what I call "sensory OOH". 

There's a tricky line to walk between gimmicky and actually engaging, but I'm already seeing brands find a good balance. 

> Starbucks in London released coffee aromas during morning rush hours, increasing dwell time by 25%.
> In Stockholm, Absolut Vodka let users mix virtual cocktails on touch-sensitive posters, increasing brand recall by 40% increase.
> AR Disney characters posed for selfies in Paris, creating viral organic reach.

There's no doubt about it. Sensory experiences stick.

#DOOH #IRL #OOH

Open article: How OOH will come into its own in 2026 – driven by the World Cup and the smell of coffee - InternetRetailing by internetretailing.net

Out of home (OOH) advertising has long been a staple of the marketing world and you may be forgiven for thinking that, in the digital era, its reach was now limited. Afterall, who wants broad-brush ads when digital can be super targeted? Everyone it would seem – now that OOH is evolving.  According to eMarketer, in […]

How OOH will come into its own in 2026 – driven by the World Cup and the smell of coffee - InternetRetailing

"We have to start paying more attention to the real world again." 

Couldn't have said it better myself, Brad. And to any OOH naysayers out there, IRL ≠ disconnected from all the tools, metrics, and KPIs we marketers love.

#IRL #DOOH

Open article: CES 2026: OUTFRONT's Head of Brand Solutions on Marketing Industry Takeaways - Chief Marketer by chiefmarketer.com

Outfront's Head of Brand Solutions Brad Alperin discusses what marketers can take away from the show, how AI is integrating into marketing processes and what new tech inspired him this year.

CES 2026: OUTFRONT's Head of Brand Solutions on Marketing Industry Takeaways - Chief Marketer

If 2025 taught us one thing about IRL, it’s that “analog vs digital” is the wrong debate.

What really mattered last year:

	•	Can we prove impact, not just assume it?
	•	Can we use data and AI to make creative smarter, not just more complicated?
	•	Can we remember that behind every impression is an actual person hurrying to work, walking their dog, or taking their kids to school?

The magic happens when technology, measurement, and creativity work together out in the physical world. That’s where IRL is at its best.

This year, I’m excited about:

	•	Better attention and outcome measurement
	•	More dynamic, context-aware creative in IRL
	•	Closer collaboration between media, creative, and tech teams

What did 2025 change in your thinking about IRL?

I'm glad to see this pointed out: IRL used to live in isolation, but not any longer. 

Now, it's designed with two audiences in mind. The people standing in front of it right now, and the thousands who’ll see it later on their phones.

The "virality" is already baked in, because IRL *is* inherently social. And the smartest brands are taking advantage of that by designing their social media strategy AROUND it, instead of the other way around.

This is why I'm a big advocate for designing creative around both screens (and both audiences).

#DOOH #IRL #OOH

Open article: Tom Stone: what happens when Out of Home thinks like social? - More About Advertising by moreaboutadvertising.com

There was something quietly revolutionary about the moment billboards stopped being billboards and s

Tom Stone: what happens when Out of Home thinks like social? - More About Advertising

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