Everything is going to be much harder than you anticipate it to be, so be prepared to see this journey not just as a professional one, but as one that will challenge you mentally, spiritually, emotionally, physically, etc.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Lee Rubin, Founder.

Lee Rubin is the co-founder and CEO at Confetti. Lee is a visionary culture leader with a decade of experience in B2B sales. She’s one of the world’s experts on remote event planning. Under her leadership, Confetti scaled from $0 to $12m in annual revenue within 2 years using only $2.5m in funding. She leads a team of 60 people who support a customer base of over 4,000 unique paying companies. On Confetti you can discover, plan and book experiences that improve culture — anything from team building and wellness to soft-skill development workshops and DE&I programs. Her hope is that Confetti not only offers a place for people to easily and quickly book these experiences, but to be a vehicle that changes the relationship people have with their jobs and the people we work with by making it more meaningful.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Iwanted to be an entrepreneur from a very young age. There seems to be no shortage of problems that this world needs us to solve and I knew I just needed to find one of them to ‘call my own’.

When I was part of the team at ZocDoc I saw how much money the company was investing in culture. The problem was that events are really complicated to plan and often the responsibility is left on one random person’s shoulders. The team found it super time consuming to come up with ideas and start reaching out to unresponsive vendors. They usually resorted to going to the bar which wasn’t really building strong, professional and authentic relationships with one another.

Eventually I thought “It would be really cool if there was one website that helped you find these activities to do with your team and book it really easily”. I left ZocDoc and did just that. I built a cute little website at first on Wix.com that had a variety of team building activities. Confetti started for the in-person world, pre-COVID so most of our experiences took place inside the offices of our customers.

At the time we had everything from in-office portable laser tag to puppy parties. I started networking and helping dozens of companies put together fun experiences. But shortly into my new career I realized something that is now core to our DNA — If I let any vendor advertise on the website some are going to be good and some are not going to be great. And for experiences that are less than amazing, it’s a waste of an opportunity to truly connect your team with one another (a privilege we take very seriously).

Can you share the most interesting story that happened to you since you began leading your company?

The best thing in terms of building this company was finding my co-founder, Eyal Hakim.

When you’re building a company at a very young age, or at any age if you’re doing it for the first time, you don’t know what the right answer is for the challenges that you are dealing with. You don’t know what you don’t know. When I first started Confetti, the bad advice I heeded was that your equity and the ownership you have within the company should be guarded with your life. I took that advice seriously and tried to build Confetti using external developers for essentially the first two years. And after pouring my life savings into it, I realized I was getting nowhere. I didn’t know how to build a tech company myself and I knew I needed to find a technical co-founder.

I interviewed over 100 people before I found Eyal. By the time that we had met, I had about five different potential co-founders that I was actively at the finish line with. They had finished their assignments and we had conducted several interviews. Then I met Eyal and I really liked him from day one. He said that he had another offer on the table himself and that he needed us to make a decision potentially within the next three days, which I thought was super tight to shake hands with someone you barely know. So, we spent a lot of time together over those three days and I finally felt comfortable. Largely driven by our seamless communication. I did have these other prospects that I spent more time with, but I weirdly didn’t have as much confidence as I did with Eyal. We negotiated the terms of our partnership and shook hands in his car and five years later, we are still co-founders. It’s an important story for people to know because he is my second half in this company and I wouldn’t want to do this journey with anyone else. Not many people know this, but the biggest reason why companies fail is co-founder blow-ups. Not competition. Not a lack of funding. But ultimately the people that you’re working with are not getting along.

I’m so glad that I interviewed so many people during my process that once I met Eyal, it was easy to know and feel that this was the right decision.

Ok and sprinkle a bit of luck :)

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

It has to be a time from the Confetti stone ages. We’ll call it Before Eyal, or BE. I was working with a freelance developer. I had no idea how to even communicate my ideas to him. When I was waiting for updates, he would tell me that the code is being deployed. Every time I spoke to him he would tell me that “the code is still being deployed.” I had no idea what he meant when he’d tell me this, yet it was almost all he’d ever say to me.I was thinking there was a heavy amount of data and software that needed to be downloaded and that it takes forever and he was just stringing me along and I never got a finished product from him. That’s also when I decided I really needed a true partner. It wasn’t until Eyal joined me that I fully understood what this meant. Now I know- thanks to Eyal- that Confetti’s code is deployed in just about 5 minutes today. If I’d tried to accomplish what Eyal and I have done in regard to our platform’s sophistication with any of the freelance developers I’d worked with previously, I’d still be waiting for the code to be deployed.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are two people. One of them is a guy called Jonathan Messika, who is the Vice President of Product at Promo.com. He was the first person that I ever really shared the idea of Confetti with and that I wanted to be an entrepreneur. He just said “you should go for it”. He was an entrepreneur at the time too. It’s easier said than done, but he pushed me, encouraged me and was there for me every step of the way. He answered all of my questions; he eased many of my fears. He let me work out of his office for a long time without collecting any rent from me, paying for one too many lunches along the way and I’m forever indebted to him for all his help during those transformative first few years.

The other person is Itamar Mula who is co-founder at a company called Acumen. He helped me as a technical adviser reviewing the resumes of the many people that were interviewing for that co-founder position. He reviewed the codes from the assigners (including Eyal’s!) and was a sounding board for all my complaints and worries. I’m forever grateful for him too. He was such an integral part in me getting to Eyal and confirming that he was the right person for me. I’ll also share that when Eyal and I met over those first few months of getting to know each other, I had trust issues. We went to work together at Itamar’s house. He told me that I needed to trust my partner and having that sit down conversation was the day that I decided to put the bad advice I’d been given previously aside. It’s served me super well to give out that trust.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

I have mixed feelings on this question, and the broader conversation that it stems from.

On the one hand, in my own experience as an entrepreneur in the tech industry, it seems pretty apparent that there is still a poor representation of females not only in my position, but in positions of influence within startups or the gatekeepers that breathe life into ideas like Confetti through investment. I know that it’s something close to ¾ of all VC firms don’t have a female partner and female founders still receive less than 3% of venture capital investments. It’s puzzling to me. Especially when you consider the research done at Harvard that shows VC firms with more female hires have been able to see 10% more profitable exits for their portfolio companies.

But I think often when we have these conversations, we lose the forest for the trees a bit. I’m definitely guilty of it. I battle with the idea of whether we will see the boy’s club dynamic that’s so common across a vast majority of society ever be dismantled. However, it’s undeniable to dismiss that there’s been significant progress in what women as a whole, across multiple generations, have been able to accomplish. One of the many crazy stats I remember hearing during the pandemic was that women accounted for 60% of all college students by the end of 2021. In the same way I think we shouldn’t accept a lack of equality as zero progress, I think so many of the steps forward taken by women will bear exponential fruit in the future. I think secondary education is a great predictor of the roles women will hold in society in the future. I don’t think it’s my job, or any other woman’s job to achieve equality for all women before we die. But I think I feel some type of responsibility to push the rock a little bit further up the hill.

I also struggle with my own interpretation of what equality means or looks like for women. As a woman, there’s parts of me that wants to be seen and treated no differently than my male counterparts. On the other hand, we’re not the same, and therefore not equal and never will be. So why should we be trying to construct a system that will treat women like men? I don’t think the answer to how to treat working women who want to be working mothers is to disenfranchise them. But I do think there needs to be an acknowledgement of the mental, physical, and emotional tole that women go through when becoming a mother. After so many years of a broken system, I wouldn’t mind seeing an overcorrection for how we treat our working moms.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

We need to be comfortable having really deep conversations with those founders and the people you want to do business with and support them. I think that we need to do a better job not just optimizing for money — our time and life is such an incredible currency and such a scarce resource, we should lead with empathy and humanity in business.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

I think some of the biggest headwinds women face within the traditional corporate career track are dealt with head on when we choose the entrepreneur route. You hear so many stories from women (young and old) that harp on not feeling heard in a meeting, or having credit taken for something they developed. As a founder, you are placing yourself in a position where the trajectory of the entire company is a result of your ideas and intuition. That’s a really rewarding feeling and the empowerment that comes with it is something that I think is unique in building your own business. I think there’s a level of pride that is only reached when you’ve taken a situation into your own hands. But at the end of the day, I think these struggles are something that anybody might face, regardless of gender.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

There are lots of misconceptions out there revolving around starting your own business. And clearing up these misconceptions isn’t easy, especially when the make-6-figures-in-30-days influencers romanticize the life of “being your own boss” to sell their class.

So many people try to sell entrepreneurship as a get-rich-quick scheme and money talks. And, honestly, it’s easy to believe if you’re only focusing on the financial success stories, like Steve Jobs or Bill Gates. Most startups aren’t profitable for many many years. The initial cash flow coming in isn’t (and shouldn’t) go into your pocket. It goes back into the business.

But successful entrepreneurs aren’t in it just for the money; they’re in it to create something special.

Starting a company exposes you to challenges you’ve never faced and roles you may not have experience in, like accounting or marketing. You’re suddenly the CEO, accountant, recruiter, HR and developer all at the same time. You’re conducting market research, creating investor pitches, finding customers, and networking your butt off.

If that’s not what you anticipate, you’re on a fast track for disappointment.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

No, I don’t think everyone is cut out to be a founder and some people go into entrepreneurship for the wrong reasons. Even founders who made the jump question whether it was the right decision and deal with pretty paralyzing mental health issues and deep imposter syndrome. It’s not easy at all.

I think to succeed though you need to develop a deep connection to the impact that you want to make and there needs to be a fuel that keeps you going that isn’t just purely based on money. You need to be agile, you need to be willing to change yourself, to listen and you need to be a true leader that can inspire change in other people. Most people hate and avoid change — you simply can’t be that kind of person as a founder.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

Everything is going to be much harder than you anticipate it to be, so be prepared to see this journey not just as a professional one, but as one that will challenge you mentally, spiritually, emotionally, physically, etc.

You’re going to have a million good ideas in your life, stay extremely focused on building that “one thing” very well and look at each project as something that should contribute to making that one thing move forward and be careful of distractions.

Surround yourself with good people. Because this journey is already hard AF and it sucks to work with @$$holes. If they don’t align with your values, don’t work with them.

Any C-Suite person should be good enough to be the CEO of your company. You should be able to trust them with their departments fully, but also be smart, flexible and capable enough to run the entire company. Ask yourself, if they were the CEO would you join their startup?

The most complex part of this journey is working with other people. We’re all so complex and different, yet we’re all so similar…So become exceptional at managing, leading, inspiring, etc.

How have you used your success to make the world a better place?

So many people look forward to Fridays and dread Mondays, and that’s such a terrible way to live. A lot of people don’t like their jobs and Confetti wants to change the relationship that people have with their jobs. We want to help companies create deeper meaning between the people colleagues and improve the work that they’re doing. If people like their team members, they communicate better — and if people enjoy their time together they’ll succeed more and solve problems better, faster.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

There are so many things that this world needs right now, whether it’s work that goes towards the climate change crisis or providing more clean water and food to those who are starving.

There are, however, only certain things that I can do within my control and if I can inspire a movement that can bring the most amount of good to the most amount of people, it’s improving the relationship that people have with their co-workers and their jobs. I choose to believe that the consciousness of the planet will improve as a result.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

If I had to choose one, it would be Brené Brown who has a podcast ‘Dare to Lead’ which I follow religiously. She talks about many of the things that are missing from the workplace and guests include genuine culture shifters that are building a more just world and that requires very daring leadership. I think she just checks all the boxes in terms of what this world needs right now.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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