Stephen and Robert Yoskowitz

Bringing ideas to life is more about discipline than inspiration, though it usually starts with one of us saying, “wait a minute!” then drawing furiously on one of a whiteboard.”


Robert Yoskowitz: Robert is one of the co-founders of Joinesty, and acts as the company CEO, guiding the company’s business strategy, fundraising, and overall vision. Prior to Joinesty, Robert was a cofounder of Two Brothers Investment Group, a hedge fund parent company, through which he developed and successfully helped run three small-scale hedge funds. Robert is a graduate of Harvard Law School, and worked for Cooley LLP in San Francisco in the Emerging Company Practice. He has his BA in economics from Haverford College.

Stephen Yoskowitz: Stephen is one of the co-founders of Joinesty, and acts as the company CFO, ensuring GAAP compliance, developing and managing the employee compensation and benefits plan, and providing counsel to the CEO on matters of strategic and operational financial planning. Prior to Joinesty, Stephen was a cofounder of Two Brothers Investment Group, where he successfully helped run three small-scale hedge funds. Before Two Brothers Investment Group, Stephen spent nearly six years as an intelligence officer for the Defense Intelligence Agency. Stephen attended Georgetown University’s School of Foreign Service, where he received his Bachelor’s of Science in International Politics.

Where did the idea for Joinesty come from?

The idea for Joinesty came about when I was at Harvard Law School, and my brother, Steve, was deployed in Afghanistan for the Department of Defense. While trying to share passwords, we realized our online accounts were about more than just passwords. One thing we noticed, was when you login to websites, it requests both an email and password, but yet everyone only talks about password security. So, we starting building a broader solution than just password management – one that not only organizes passwords, but also helps users stay private by masking their email address, as well as protects inboxes and identities from hackers and spammers.

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

Each week we have a coordination meeting to ensure everyone is aligned on that week’s goals and deliverables, with daily team check-ins as needed. To ensure productivity, we define deliverables and then give our teams the autonomy to do their own work, while we work in the background to ensure everything runs smoothly. To help with focus, we have a screenless culture where we try not to check our emails more than four times a day, and have a strict “closed computer” policy during meetings, other than a single note-taker. Thanks to this, everyone is able to stay focused.

How do you bring ideas to life?

Bringing ideas to life is more about discipline than inspiration, though it usually starts with one of us saying, “wait a minute!” then drawing furiously on one of a whiteboard. When we have an idea, we set aside time to raise it with the relevant team for open questions, and then we part ways and come back later for a “murder board” session once everyone has had time to think on it. During this session we focus on defining two key items: (1) the resources required to bring this idea into the world and (2) the value of doing so. If the value outweighs the resources needed, then we review the requirements, and team members self-select based on skill set, interest, and availability to deliver a solution.

What’s one trend that really excites you?

We’re very excited by the trend of everyday people realizing that online privacy and security aren’t just for “tech nerds,” but rather something that affects all of us. The fact is, no matter who you are, your identity is not something to be handed out, traded or sold. Seeing people perk up when you mention online privacy and protection makes us happy.

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

One of the most difficult habits to get into is true division of labor because it relies on trust. Entrepreneurs have a tendency to not trust others to execute their vision, resulting in them becoming overwhelmed and unfocused. By trusting those you work with to execute the right idea, you gain scale efficiencies as your time is freed up to focus on each one more intently and execute more efficiently.

What advice would you give your younger self?

Validate early, validate often, and don’t get hung up on things that you don’t credibly think will impact customer growth, retention, and lifetime value to you as a business. Components will be fluid, so it’s important to just get the product in front of customers to not only see what they like and don’t like, but also how they use the product.

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

There are always the same four costs associated with using any product, but everyone weighs them differently: Money; Time; Effort; and Risk (of use). No product has the same matrix, so the trick is to identify which of these variables most impacts your particular users and work hard to decrease that sum in relation to the value of the product. The most successful products are not always the cheapest or the easiest, but they are the ones that the the greatest perceived net value against the drawbacks.

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

Constantly view your product as broken and in need of improvement. The minute you let moss grow, an innovator will come around ready to take you out. Additionally, always ask your users what they think of your platform and what they’d like as an improvement. At the end of the day, you can have a vision for your product, but the product isn’t for you, it’s for your users.

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

Taking every meeting that comes and talking with everyone who is willing to hear our ideas. We have a contract with an enormous investor company in Germany all because we started chatting about our product with a random businessman at a cocktail hour in Berlin.

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

We spent months trying to get a B2B partnership. However, we never identified firm deadlines and benchmarks, so the process continued without defined steps to officially get the relationship approved. Eventually we stepped up and provided a clear path to finalization, despite potentially alienating the partner. Luckily, it ended up being the opposite and the whole relationship benefited us taking the initiative to outline those steps forward.

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

Make a reliable conferencing platform that operates off a single, shareable link, with a time expiration, and allows video and screen-sharing without any downloads. There are many attempts out there to solve collaboration with increasingly remote teams and no one has hit the nail on the head yet.

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

A Calendly subscription for everyone on the team. A huge time waster and mental strain is handling back-and-forth logistics for simple things like meetings, so the ability to just send out a link and automatically have meetings set up has been a game-changer for us in terms of the stress of coordination and logistics. We now have meetings automatically pop into our calendars, without the dozens of back-and-forth emails that we used to deal with.

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

Our #1 tool here is Calendly. However, if I had to choose another one, it would be Trello – it’s very intuitive and allows everyone to have clearly defined tasks and deadlines.

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

Traction” by Gabriel Weinberg, the founder of DuckDuckGo. It’s a brilliant breakdown of the different ways a business can achieve user growth and a must read for anyone who wants to understand the different ways a business can acquire customers.

What is your favorite quote?

“The value of an idea lies in the using of it.” It’s a quote by Thomas Edison, who, established businesses that are still relevant in modern society. It’s a quote that is the foundation of any business – understanding the use case for your product.

Key learnings:

  • Online privacy is a concern that will only grow in importance and significance, so figuring out ways to protect your online identity is crucial
  • Understanding your users and how they want to use your product is vital to getting customer adoption and retention
  • Have conversations with anyone who is willing to listen to your idea – you never know where it’s going to lead
  • Put a full-faith effort into your chosen growth channels, but it’s also important to cut them loose if they aren’t going to be the best return on your investment of time, effort, and money


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