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In our sixth edition, we speak with Raj De Datta — CEO and co-founder of Bloomreach. The Bloomreach 14-year journey epitomizes the ups and downs of startup life. The first and last six years were marked by notable growth, akin to a rocket ship’s ascent. However, the middle phase, about three to four years, was tough, representing the inevitable challenges all technology companies face. Yet, Bloomreach’s rebound in the recent years underlines the importance of resilience and determination in overcoming obstacles and achieving success require to build a category-defining company.

Here are the top lessons founders can learn from Raj’s journey building Bloomreach over the past 14 years.

#1: Give yourself as many chances to fail as possible.

“We actually were able to get $5 million in the bank pretty early, but we only had five or six people in the company for the first, probably 18 months, so we didn’t hire a lot of people. And the thesis behind that was the key to solving really hard problems is to have the right people, but also to give yourself the room to fail a bunch of times. And so we were able to put the triangle together between right people, big vision and money and then be able to iterate on that for a long period of time until it really came together.

💡Actionable takeaway: In the early days, avoid over hiring in order to extend your runway and create as many opportunities to iterate your way through failure until you find product market fit. 

#2: Downturns are the best time to start. 

“The best time to start in my mind is in the worst economic times. That sounds like a weird thing to say, but when you want the good economic times is when your venture is like hitting on all cylinders and that usually takes a few years. So often what happens when you start in the best times is money is plentiful, but people are hard to hire. It’s really expensive, it’s a lot of competitive noise out there. So only one out of the like, ten things you need to start a successful venture is easy and that’s getting money. The other nine are actually pretty hard in good economic times.”

💡Actionable takeaway: Don’t let all the negative news about the economy and decline of venture funding deter you from starting your company. Money is just one piece that you need to get right to build a category-defining company. Focus on those other pieces. 

#3: Be brutally honest with yourself about the long term viability of your product. 

“We had a first product that really was, like, selling really well, but was kind of a mirage. It wasn’t going to last. So around 2015, it was really clear that this business that we had built, which by then had probably 150 to 180 people, was not going to last. And so we had two choices.

We either could shut the whole thing down, despite the fact that it had this early success, or we could build a completely new business on the same tech and on the same value proposition and on the same vision and with the same cultural roots. And that’s what we chose to do. And so what was so difficult about, like, as you call it, the messy middle, was sort of, like, had a business that was declining and having to build a brand new startup, largely in 2015, 2016, that was almost at ground zero, and build that to what Bloomreach is today.

And if I look at what Bloomreach is today, which publicly we’ve announced is more than $150,000,000 of annual recurring revenue, and I think about that original business that we had in 2015 or 2016, like a million dollars of it is from that original business. The rest of it has been built in the last six years.”

💡Actionable takeaway: Don’t assume that just because a product is working today that it will continue to work 5-10 years from now. Be prepared to give up what’s good for the opportunity to pursue something that can be great. 

#4: Be honest and transparent with your team about where you are. 

“I remember standing up in front of a room of people back in 2015, 2016, saying, look, we have this business. It’s in decline. It’s kind of not looking good, frankly. But we have a lot of incredible assets. We have great tech, we have great customers, we have a great culture and a great group of people in this room. And I don’t know how long it’s going to take for us to go build something new that creates an incredibly valuable company. But what I know is, I’m here, we’re here. These are our assets. If you want to be on this journey with me, stick around, and I won’t fault you if you don’t. “

💡Actionable takeaway: Be fully transparent and honest with your team about where you are as an organization. This honesty may lead to some team members leaving but those who stay will be more bought in than ever before to rally around whatever needs to be done. 

#5: Be prepared to go all-in.

“What I told myself was, look, you just got to stop thinking about whether you want to do this or not. That’s not fair to your investors or to the people on the team. I either have to be all in or all out, but there is no in between. And so I almost told myself, look, I’m just not going to think about whether this makes rational sense. I’m just going to make it happen. And until the day when I give up making it happen, I’m just going to be 100% all in and convey that. And that was really important as well because me being so all in caused a few other people to be all in, who caused a few other people to be all in. And we pulled it off.”

💡Actionable takeaway: Before you can expect your team to go all in, have an honest conversation with yourself and make sure you are prepared to do the same.

#6: Always give back to the entrepreneurial community.

“I see it as my responsibility. I’ve been an entrepreneur for 25 years, and I do think there is a glamorization of the profession that suggests that everything looks like Elon Musk or whatever it is. Mark Zuckerberg. And those aren’t the stories of the 99%. And I really want to make sure that we tell the real story that we give people the courage to start these businesses and confront the obstacles that come along the way. And if my story helps motivate people and be motivated for the right reasons, then I feel like it’s part of my responsibility, to give back to the entrepreneurial community the way others gave to me.”

💡Actionable takeaway: As you experience different levels of success, remember to take the time to give back to entrepreneurial community by sharing what you’ve learned from your own journey.