Building a $30M/yr portfolio after an 8-figure exit

Less than a decade ago, Jesse Pujji saw an opportunity and built an agency around it. He recently sold that agency — Ampush — for mid-eight figures while it was managing over $1 billion in ad spend.

Now, he's using that money to build a venture studio. And the three products in his portfolio are already bringing in $30M per year.

Here's Jesse on how he did it. 👇

$1 billion in ad spend

I'm a founder and investor passionate about empowering individuals through entrepreneurship. My journey began with bootstrapping my first venture, Ampush, which culminated in a successful mid 8-figure exit.

During that time, we navigated the complexities of managing over $1 billion in digital media spend, scaling to a team of more than 100 employees, and collaborating with prominent brands like Uber, Birchbox, and Hulu. This experience, a true rollercoaster, laid the groundwork for my current endeavors.

Today, I channel my expertise into building ambitious, bootstrapped companies through my venture studio, Gateway X.

Our portfolio is now making $30M/yr and includes:

• Growth Assistant, which integrates top-tier offshore growth marketers into businesses.

• Aux Insights, providing digital marketing due diligence and value creation for private equity.

• Unbloat, a direct-to-consumer brand offering doctor-formulated gut health supplements.

Beyond venture building, I share insights on sales, finance, hiring, and more in my weekly newsletter, Bootstrapped Giants.

Curiosity and ambition

My entrepreneurial journey with Ampush began with a blend of youthful curiosity and ambition, sparked during my time at Goldman Sachs. While the prestige was undeniable, I yearned to build something tangible.

Conversations with my college roommates, Nick and Chris, ignited our fascination with Facebook's burgeoning advertising platform. At 25, we saw an untapped potential in pioneering performance marketing on this new frontier. It wasn't a meticulously planned venture, but rather a leap into the unknown, driven by the thrill of exploration.

We validated our idea through a scrappy, hands-on approach, running small ad campaigns for local businesses and experimenting with Facebook's capabilities. The promising results quickly revealed the scalability of our concept. Landing Uber as a client marked a pivotal moment, validating our vision and execution prowess.

From the outset, we bootstrapped the business, leveraging my modest savings from banking. We operated lean, working from a small apartment and reinvesting every earned dollar. The combination of early successes, the sheer excitement of creation, and a touch of serendipity provided the foundation for Ampush's growth and subsequent endeavors.

Building a scrappy foundation

Building the initial product for Ampush was an exercise in resourcefulness and focus. We started with minimal capital — just $100,000 pooled from my savings and those of my cofounders. This was supplemented by credit cards, which we used liberally to cover early expenses like laptops, software, and ad spend

Time was our most valuable resource, and we worked relentlessly, often clocking 80-hour weeks to get things off the ground. The skills we brought to the table were complementary: I focused on sales and strategy, Nick handled operations, and Chris tackled the technical aspects. Together, we had just enough to build a scrappy, but functional foundation.

From concept to execution, it took us about six months to get our first campaigns running and start generating revenue. We deliberately kept the scope narrow, focusing on Facebook ads because we saw its potential as a game-changing platform for performance marketing.

Instead of building complex software upfront, we started with manual processes and simple tools to test our ideas. This lean approach allowed us to iterate quickly and adapt to what worked. For example, we initially targeted small local businesses but quickly pivoted to larger clients like Uber when we saw the scalability of our model.

An evolving stack

We built a tech-enabled platform at Ampush that was primarily used internally to supercharge our performance marketing services. It wasn’t a standalone product we sold to customers, but it was a critical piece of our value proposition. The platform helped us manage and optimize massive ad spends. It allowed us to scale campaigns efficiently, analyze data in real-time, and deliver results that outperformed what most in-house teams or other agencies could achieve.

Our tech stack evolved significantly over time to meet the demands of scaling and staying competitive. Early on, we didn’t overcomplicate things — we used PHP and MySQL for the back-end and basic HTML/CSS for the front end. The focus was on speed and functionality rather than perfection.

As we grew and started managing larger ad budgets for clients like Uber and Dollar Shave Club, we transitioned to more robust frameworks like Python and Django on the backend to handle complex data processing and analytics. On the front end, we adopted React to improve user experience and make our tools more dynamic.

One of the biggest technical challenges we faced was integrating with Facebook’s rapidly changing API. Their updates often broke our systems, forcing us to adapt quickly.

Another hurdle was building scalable infrastructure to process billions of ad impressions and clicks in real-time. We eventually moved to cloud-based solutions like AWS to handle the load and ensure reliability. These changes weren’t just about keeping up — they were about staying ahead in a fast-moving industry where milliseconds and insights could make or break a campaign.

The evolution of our stack was a direct reflection of our growth and the increasing complexity of our clients’ needs.

Bake-offs and culture fails

The biggest challenges I faced at Ampush were tied to scaling the business and navigating the emotional rollercoaster of entrepreneurship. One of the hardest lessons came from a period in 2016 when we realized our once-dominant Facebook ad strategies were no longer effective.

Facebook’s algorithm had evolved, and our manual bidding and hyper-targeting methods were suddenly obsolete. We got blindsided in a bake-off with another agency, where their customer acquisition cost (CAC) was half of ours. It was a wake-up call that forced us to rethink everything.

We had to pivot quickly, invest in new tools, and embrace Facebook’s automated systems rather than fight them. It was humbling, but it taught me the importance of staying adaptable and never getting too comfortable with what’s working today.

Another challenge was around hiring and culture. Early on, we made some poor hiring decisions by prioritizing technical skills over cultural fit. This created friction within the team and slowed us down. Over time, I learned that hiring people who align with your values and vision is just as critical as their technical expertise.

Align your incentives

Ampush’s business model was rooted in performance-based marketing. We made money by managing ad spend for clients and taking a percentage of the revenue we generated for them. This aligned incentives perfectly — if our campaigns performed well, we made more money, and so did our clients.

Revenue growth was driven by a combination of factors:

• First, we focused on landing high-growth clients in industries like ride-sharing and subscription services, where our performance marketing expertise could have the biggest impact.

• Second, we constantly refined our pricing model. For instance, we introduced minimum fees to ensure profitability on smaller accounts and incentivized larger clients to scale their spend with us.

• Third, we invested in building proprietary tools and processes that improved campaign performance, which helped us retain clients and justify higher fees. By the time we sold a stake to Red Ventures, Ampush was generating mid-eight figures in annual revenue.

For aspiring entrepreneurs, the biggest takeaway here is to align your business model with your customers’ success. When your incentives are tied to delivering results, it builds trust and long-term relationships.

Snowball growth

At Ampush, attracting users and growing the business was all about leveraging the right platforms, building trust, and delivering results.

Network

Early on, we focused heavily on Facebook ads because we saw its potential as a game-changer for performance marketing. Our first clients came from cold outreach and personal networks — friends of friends who were running small businesses. We’d offer to run campaigns for free or at a steep discount, just to prove what we could do.

Once we had a few success stories, we used those as case studies to pitch larger clients. This snowballed into landing big names like Uber and Dollar Shave Club, which gave us credibility and opened doors to even more opportunities.

Partnerships

Partnerships were another key driver of growth. Facebook itself became a critical partner, but it wasn’t easy. Early on, we weren’t on their “special” partner list, which limited our access to resources and support. We had to hustle to prove our value, aligning our goals with theirs and demonstrating how we could help them grow their ad ecosystem. Once we earned that designation, it gave us a competitive edge and made it easier to attract clients.

Content

We also invested in content and thought leadership. I’d write about our strategies and successes, sharing insights on platforms like LinkedIn and industry forums. This not only attracted potential clients, but also helped us recruit top talent.

Word of mouth

Word of mouth played a huge role too — when you deliver measurable results, clients talk. Uber, for instance, was a massive referral engine for us because of the scale and success we achieved with them.

Advice: Channels, testimonials, and retention

For aspiring entrepreneurs, my advice is to focus on one channel or strategy that aligns with your strengths and double down on it. Don’t try to do everything at once.

Also, leverage social proof — whether it’s testimonials, case studies, or partnerships — to build credibility.

And remember, growth isn’t just about acquiring users, it’s about retaining them. Deliver results, and the rest will follow.

Parting advice

Land and expand

If you’re just starting out as an indie hacker, my top advice is to narrow your focus.

One of the biggest mistakes I see is people trying to serve everyone and solve every problem. It’s tempting to cast a wide net, but the truth is, the more specific you are about your Ideal Customer Profile (ICP), the faster you’ll grow.

Think about it: Amazon started with books, Facebook started with colleges, and Apple started with just computers or the iPod. Every great business begins by owning a niche and expanding from there. Find your “Nathan” — that one customer type you can serve better than anyone else — and double down on them.

Guess and test

Another key tip is to embrace the guess-and-test mindset. Early on, you don’t need everything figured out. Start with a hypothesis about who your ideal customer is, test it, and iterate based on what you learn.

For example, when we launched Growth Assistant, we initially targeted a broad range of customers, but we quickly realized that mid-sized, growth-focused companies in e-commerce and tech were our sweet spot. By narrowing our ICP, we reduced churn, improved customer satisfaction, and scaled faster.

Get the reps in

I’d recommend The Lean Startup by Eric Ries for its emphasis on testing and iteration, and Managing the Professional Service Firm if you’re in a service-based business.

But honestly, the best resource is just getting reps — putting your product or service out there, learning from feedback, and improving.

And remember, it’s not about doing everything perfectly, it’s about staying adaptable and relentlessly focused on solving real problems for your customers. That’s how you win.

Build relationships

Don’t underestimate the power of relationships, either. Your first customers will likely come from your network, so don’t be afraid to reach out to friends, former colleagues, or even cold email people in your target market.

Offer value up front — whether it’s a free trial, a discounted service, or just helpful advice — and use those early wins as case studies to build credibility.

Delegate sooner

I struggled with delegation. For years, I tried to do too much myself, which led to burnout and bottlenecks. It wasn’t until I let go of low-risk, high-time tasks and started empowering my team that we really hit our stride.

Keep a close eye on margins

In a service-based business like ours, managing costs and ensuring profitability on every account was critical to scaling sustainably.

Dream big

Dream big, but stay grounded in execution. Goals are only as good as the systems you build to achieve them.

What's next?

My goals for the future revolve around scaling Gateway X into a billion-dollar venture studio while staying true to the bootstrapped ethos.

On the business side, I want to grow each portfolio company — Growth Assistant, Aux Insights, and Unbloat — into category leaders. For example, Growth Assistant is already at eight figures in revenue, but the goal is to double that while maintaining high customer satisfaction and retention.

Aux Insights is still in its early stages, but I see massive potential in expanding its private equity partnerships and becoming the go-to for digital marketing due diligence. Unbloat, as a DTC brand, has a clear path to scaling by expanding its product line and tapping into new customer segments.

Personally, I’m focused on balancing growth with sustainability. One of the biggest lessons I’ve learned is that time is the most valuable resource. I’ve committed to only launching one new venture per year to avoid spreading myself too thin. This means being ruthless about prioritization and saying no to distractions, even when they seem like exciting opportunities.

I also want to continue growing Bootstrapped Giants as a platform for sharing knowledge and inspiring other entrepreneurs. The goal is to turn it into a self-sustaining business that can amplify its impact without burning me out.

Dive deeper

You can dive deeper into my world and learn more through several channels:

• Subscribe to the Bootstrapped Giants Newsletter to join 25,000+ founders and operators learning from my tactical advice and frameworks.

• Follow me on X for quick, actionable tips, personal reflections, and updates on my ventures.

• Connect with me on LinkedIn for professional updates, thought leadership posts, and insights into the entrepreneurial ecosystem.

• Learn aboutGateway X. We don't have a public-facing site but you can check out Growth Assistant, Aux Insights, and Unbloat.

• I’ve been featured on podcasts like My First Million and newsletters like The Hustle. These are great resources to hear more about my journey and the lessons I’ve learned along the way.

Feel free to connect with me about bootstrapping, growth marketing, e-commerce, leadership, or even a friendly game of tennis!