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Benjamin Yoskovitz: Highline Beta’s Journey in Venture Studios and VC

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Meet Benjamin Yoskovitz, the Founding Partner of Highline Beta, a hybrid venture studio and VC firm.

With a rich background in starting companies, angel investing, and authoring the book Lean Analytics, his journey is a testament to the power of innovation, resilience, and strategic thinking.

Early Beginnings

Benjamin’s entrepreneurial journey began in 1996 when he co-founded his first company, a web agency. “I fell into being a founder almost by accident,” he recalls. This initial foray into entrepreneurship set the stage for a career marked by continuous learning and adaptation.

Over the years, Benjamin has started several companies, each experience adding to his wealth of knowledge and expertise.

Highline Beta

As Ben describes it, Highline Beta is a “hybrid venture studio and VC firm” born to speed up and improve startups’ initial critical phase of getting from 0 to 1.

They specialize in technology/software startups. They work closely with corporate partners to identify growth opportunities, spin out startups, and work directly with founders from pre-incorporations to build and launch new companies.

The business model combines consulting and leveraging the equity earned in startups they build and invest in, striking a balance between immediate consultancy revenues and long-term equity gains.

A Day in the Life

Running a business as innovative as Highline Beta requires a clear division of responsibilities, especially when you have a co-founder.

Benjamin and his co-founder, Marcus Daniels, have found a way to split their duties effectively. Marcus, acting as the CEO, leads overall operations and the venture capital parts of the business.

On the other hand, Benjamin focuses on working with founders in the studio, building their MVPs, and getting to market.

Ben Yoskovitz Headshot
Benjamin Yoskovitz, Founding Partner of Highline Beta

A typical week for Ben is anything but typical. Between juggling numerous projects, strategizing for the future, and getting down to the nitty-gritty of product roadmaps and prototype testing, his schedule is a testament to the multitasking and flexibility required in such a dynamic role.

Tools of the Trade

For Benjamin Yoskovitz and his team at Highline Beta, leveraging the right technologies is crucial for maintaining efficiency and fostering innovation. Here are the essential tools they use:

  • Slack: Internal communications, keeping the team connected and informed.
  • Google Drive: Central repository for documents and files, enabling seamless collaboration.
  • Zoom: Virtual meetings with remote team members, investors, and startup founders.
  • Miro/Mural: Brainstorming, strategy sessions, and mapping out user journeys and product roadmaps.
  • Webflow: Building and testing landing pages and websites quickly and efficiently.
  • Facebook/Instagram Ads: Testing value propositions and reaching target audiences.
  • Google Ads: Occasionally used for market validation and advertising.
  • Zapier: Integrating digital tools and automating workflows to reduce manual work.
  • Heap: Analyzing website and web app performance to understand user interactions and behaviors.

These tools form the backbone of Highline Beta’s operations, enabling them to execute their unique business model efficiently and effectively.

Growth Strategies That Work

When it comes to growing the business, Ben emphasizes the importance of thought leadership, especially in an emerging area like venture studios.

Through newsletters and social media, particularly LinkedIn, he shares valuable insights from years of experience, positioning Highline Beta as a leader.

“Venture studios are gaining considerable popularity, so we’re trying to be at the forefront of that.”

Benjamin Yoskovitz

Moreover, according to Ben, the significance of in-person interactions and building trusted relationships cannot be understated. These elements have been instrumental in cultivating lasting partnerships, attracting investors, and ultimately driving the business’s growth.

Challenges and Achievements

Overcoming Failure: The Standout Jobs Story

Benjamin Yoskovitz’s entrepreneurial journey has been filled with challenges, but one of the most significant was the failure of Standout Jobs, a recruitment technology company he co-founded in 2007.

Despite raising $1.8 million, the company struggled to find its product-market fit and eventually had to sell its assets in 2010. “That was eye-opening and brutal,” Benjamin recalls. As the CEO, the experience was particularly tough, leaving a lasting impact on him.

One key lesson Benjamin learned from this failure was the importance of validating a real problem before investing time and money into building a product.

“Don’t waste your time and money building things people don’t want.”

Benjamin Yoskovitz

This experience has shaped his approach to entrepreneurship, making him laser-focused on helping the startups in Highline Beta’s portfolio avoid similar mistakes.

He now believes in systematically building companies, combining science and art, while acknowledging that luck also plays a role.

Milestones of Success: From Year One Labs to Highline Beta

Benjamin’s career is also marked by several significant achievements. One of the highlights was co-founding Year One Labs, an early-stage accelerator, in 2011-2012. This was during the rise of the Lean Startup methodology, which they applied to the companies they built.

One of the startups from Year One Labs, Localmind, was acquired by Airbnb, an experience Benjamin describes as amazing, especially seeing the founders succeed inside Airbnb and eventually the company go public.

Another notable achievement was his role as VP of Product at GoInstant, a very early-stage startup that Salesforce acquired just two years after its inception. This acquisition was a significant milestone in Benjamin’s career.

In addition to these roles, Benjamin has made 17 angel investments, some of which failed and others very successful. Helping other founders achieve their dreams has always been his passion.

Today, Highline Beta, the venture studio and VC firm he co-founded, is about eight years old and thriving. “Survival is an achievement, as long as you believe there’s a chance of growing and winning,” Benjamin notes. He looks forward to the next decade, eager to see how things will evolve and continue to grow.

Advice for Aspiring Entrepreneurs

Ben has straightforward advice for those considering the entrepreneurial path: “Do it.”

“Do it.”

Benjamin Yoskovitz

He believes entrepreneurs are essential for solving the world’s problems and creating the products and services we rely on daily. However, he also emphasizes the importance of a realistic and methodical approach.

While entrepreneurship can be incredibly rewarding, Benjamin cautions against romanticizing the journey. “Don’t put yourself into complete financial ruin,” he advises. Entrepreneurship is hard, and it’s not always a wonderful experience. But if people don’t leap, we miss potential innovations and solutions.

For those ready to jump in, Benjamin recommends applying rigorous methods to validate your business ideas. Techniques like Lean Startup, Design Thinking, and Jobs to Be Done can provide a solid framework for ensuring you’re solving a real problem.

“Don’t just build a product and hope people will pay for it. Do your homework,” he stresses. Too many founders skip the crucial step of upfront research, only to find out later that no one cares about their product.

Benjamin also warns against getting caught up in the hype of celebrity founders and massive VC funding. “It’s easy to get enamored with companies raising millions of dollars, but that’s not the only way to be an entrepreneur,” he notes. The key is to be methodical and thoughtful about how you build your business.

So, if you’re considering becoming an entrepreneur, Benjamin’s advice is clear: Jump in, but do it thoughtfully and methodically.

Benjamin Yoskovitz’s Lightning Round

In this lightning round, I asked Benjamin Yoskovitz to answer 13 rapid-fire questions:

What’s something that’s in your pocket right now, besides your phone?

A wipe for my glasses. Any smudge on my glasses drives me crazy. Talk about exciting. 🙂

Artificial intelligence: hope or dread?

Hope. Will people misuse and abuse it? Of course. But overall I choose hope.

Your favorite place to think big?

Everywhere. Some part of my brain is always thinking big, even if it’s doing so behind the scenes. You can’t win as a founder without ambition.

If you were out of business tomorrow, what job would you pursue?

Running product at a startup. I love building products, and so I’d probably choose to dig in on one. But eventually I’d start something else.

One object from your childhood you could never throw away?

Pictures of my brother. He passed away when we were very young (he was 8 and I was 10). I have a few of his things as well that I hold onto.

One feature you wish your phone had?

Why does Siri suck so bad? It makes no sense. Also, I wish it would self-clean itself so it wasn’t covered in germs.

Your favorite mobile app?

Puck Drop. It’s an NHL simulator game. Insanely fun. Closest thing to being a GM of a team that I’ll ever be.

The book that most influenced you?

I’m picking 2: Lean Startup by Eric Ries and Four Steps to the Epiphany by Steve Blank

Messy desk or clean desk?

Can I go in the middle? 🙂 I’d say my desk is reasonable clean, but it’s a perpetual battle.

One thing you always have in your fridge?

Non-alcoholic beer, b/c I gave up drinking many years ago. Still have the occasional alcoholic drink, but very rarely.

The most creative measure of success you’ve set for a team?

Number of street interviews in an hour. Entrepreneurs don’t always like talking to people, so we push them to get on the street and interview strangers. If they can do that, they can do pretty much anything.

Your favorite time-saving hack?

Work harder. I don’t know what to tell you. Some people spend more time trying to optimize productivity than just doing the work that needs to be done.

Best movie ever?

Honestly, I don’t have one or care. But forced to pick, right now, I’ll say The Avengers. “That’s my secret, Cap: I’m always angry.” Damn.

Join the Journey

Benjamin Yoskovitz’s journey through entrepreneurship is inspiring and filled with practical insights and wisdom gained from years of experience.

Subscribing to Ben’s newsletter, Focused Chaos, is an excellent way to stay connected and learn more about and follow his thoughts on entrepreneurship, product management, analytics, and more.

You can also follow Ben on LinkedIn and Twitter (X).

We hope this interview has provided you with invaluable insights into the world of tech entrepreneurship and venture studios. Stay tuned for more inspirational stories from other remarkable entrepreneurs in our series.

A special thanks to Startup Shinobi for introducing us to Benjamin Yoskovitz.

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