Roi Chobadi

Entrepreneurs can’t afford vagueness or not saying things exactly as they are, even when they are uncomfortable.


Roi Chobadi is a serial deep-tech entrepreneur and currently the co-founder and CEO of STELLARES, an AI platform that helps top tech talent manage their career and find unique, tailor-fit opportunities beyond their personal network; it also helps companies recruit top technical talent.

Previously, Roi co-founded LiquidM, an ML SaaS big-data mobile advertising management platform, where he led the product, marketing, and tech departments, managing a talented team of 40 individuals. Roi co-led LiquidM to its acquisition by Ligatus in 2016.

Roi started his career in IDF Unit 8200 (Israel’s NSA equivalent) and has 20 years of programming experience. Roi earned his MBA at Stanford University and holds three bachelor degrees — in law, physics, and electrical engineering — from Tel Aviv University. Roi is the founder and co-president of the 8200 alumni Association in Silicon Valley and the co-founder and partner at profounder, a Palo Alto-based micro VC focused on seed investments.

Where did the idea for your company come from?

The idea for STELLARES came from a combination of a few factors. When I was heading product/tech/marketing at LiquidM, hiring was my No. 1 challenge, and it occupied my thoughts constantly. I recognized the market was broken, with too much asymmetry of information, friction of discovering information, and friction of connecting beyond networks. I knew there must be a better way than the current broken tools and processes!

As head of the 8200 alumni in Silicon Valley association — where hundreds of the world’s top engineers and technologists are members — I constantly found myself advising really talented people on their careers. I found it so interesting that the challenges weren’t trivial on the talent side, either.
I realized I’m actually uniquely positioned to solve this problem. LiquidM built deep machine learning technology to match a person to a product/service he or she is most likely to buy. Why couldn’t we take advantage of the advertising industry’s most cutting-edge machine learning technology know-how and use it to match people to other people, projects, challenges, or cultures instead of to products?

What does your typical day look like and how do you make it productive?

A typical day includes meeting with STELLARES managers each for 15 minutes, as well as several meetings with customers or other stakeholders and some time to think and create. I keep it productive by being very intentional about how much of my time goes where. Every time I sit down to do something, I know the objective and how it connects to the larger goal (the weekly, quarterly, and big picture); it’s all about prioritization and time allocation. I don’t get distracted or sucked into chasing butterflies.

How do you bring ideas to life?

I think them through, play devil’s advocate, research, and talk to industry leaders familiar with the problem these ideas are attempting to address. Feedback, collaboration, and brainstorming are key. Prioritization or focus is critical as well — what is really the essence of the idea, and what are all the nice-to-haves around it? To execute, I build a tree of prioritized objectives, each built from prioritized activities, and so forth. Each activity should have a clear cost, benefit, and risks analysis, and these should be evaluated to determine which should be done, how well, and in what order.

What’s one trend that excites you?

Personalization. We’re moving from leveraging technology for mass production, mass marketing, and mass consumerism into leveraging technology for true personalization, recognizing the uniqueness in each and every one of us and tailoring any experience to it. It’s not just about celebrating individualism; it is also about re-creating communities based on shared values/styles/preferences — this time, not arbitrarily/randomly (like where you were born), but more fundamentally (like what makes us tick). STELLARES is driving the career management side of this trend, finding just the right job for each individual.

What is one habit of yours that makes you more productive as an entrepreneur?

Ruthless and crystal-clear prioritization and control of my time and energy and radical honesty and directness with everyone I work with. Entrepreneurs can’t afford vagueness or not saying things exactly as they are, even when they are uncomfortable.

What advice would you give your younger self?

Take more time to think and carefully choose the problem to solve before going and solving one.

Tell us something that’s true that almost nobody agrees with you on.

Amongst many other things, a good leader must be her or his team members’ psychologist and care for their well-being in work, outside of work, at work, and as a result of work.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Ask people how they feel (and really mean it), and go as deep as necessary to understand them. Some people might overwork themselves without noticing. A leader should call that out and ask the person to take a break. Other people might feel unappreciated or like they’re not progressing; if that feeling sticks with them, you might lose an amazing team leader who could have stayed to have a great career and journey. A leader’s job is not just to manage the team’s output, but also to truly care about their well-being and be there when they need him/her, even when he or she isn’t sometimes consciously aware of it. Care for your team!

What is one strategy that has helped you grow your business?

Make decisions based on data. Some problems seem huge, but data implies they are actually not. Others might be overlooked, but data implies they are huge. Always collect data, structurally, and then review it and take action based on it.

What is one failure you had as an entrepreneur, and how did you overcome it?

Solving the wrong problem is entrepreneurs’ No. 1 enemy. I’ve done that before. You need to be very honest with yourself and others and always re-examine — ask, “Am I solving the right problem?” and pivot as needed. Also, always make sure you get the question right first. Then, you come up with the solution. Too many people start with solutions that seem smart, without really getting to the bottom of the question or problem they are trying to solve.

What is one business idea that you’re willing to give away to our readers?

Mobility between workplaces is further and further increasing. Some of the assets gained by an employee belong to the organization (IP, customers, etc.), while others also belong to the individual (learnings, relationships, etc.). I’d love to see a solution that helps an employee extract his or her individual assets and take those to the next job. That way, that person can keep building on the value he or she has created personally while also creating value for the employer.

What is the best $100 you recently spent? What and why?

My team was stretched, so I utilized cheap labor marketplaces such as Fiverr to save them time on mundane work (e.g., lead generation, data validation, or any type of automation).

What is one piece of software or a web service that helps you be productive?

Calendar. Everything I do is an object on my calendar — not just meetings, but also my time with myself. Everything has a duration and goal. Color-coding helps me easily decide which activities to move when I need flexibility.

What is the one book that you recommend our community should read and why?

“The Hard Thing About Hard Things” by Ben Horowitz is a great book. It helps an early-stage entrepreneur see things as they are and get into the right mindset.

What is your favorite quote?

“On average, a human being has one testicle.” It reminds you to be careful with jumping to conclusions and generalizing. Many times, the answer lies two layers deeper than where you currently are, and if you stay on the superficial level (“How many testes does the average human have?”) without thinking through different use cases (gender), you may reach an entirely wrong conclusion. How do you know if you are at the right level? Always “sanity test” your conclusions. “Does this make sense to me?” “Is that what I’d expect it to be?” “What else might be going on here?”

Key Learnings:

  • Be intentional about where your time goes. Control your time, and don’t allow it to control you. Each activity should have a clear objective and time frame. A calendar can be used to plan and frame all activities.
  • Always do your best to use data in decision-making. Data can’t make the decisions for you, but you always must collect data and consider it when making the decision.
  • Be very honest and direct with everyone you work with. Share your thoughts as they are and invite others to do so.
  • Care for your team. Don’t shy away from personal discussions about their well-being and “being their psychologist.” If you are leading people, by definition you already are responsible for their well-being, so it’s best to own it. Don’t expect openness from your team members if you’re not open with them yourself.
  • Be careful about jumping to conclusions and generalizing. Many times, the answer lies two layers deeper than where you currently are.