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What I wish I knew for Year 1 of my Startup: 13 Founders Reflect on Lessons Learned

Things we wished we knew during the first year of our startups

John Joseph, CEO, Datanomix

While not exactly in this company and not super profound really, the voice of the customer is so informative if you are listening. If you want to build something people will love, then you need to spend some time in their heads. Set aside the time to speak with them about the problems that they see getting in the way of greater success. Understand why these are problems in the first place. You will quickly learn that your customers are very smart, resourceful and passionate. That’s how they got to where they are today.  Those customer inputs will serve as the magnetic compass for your development teams. You may think you know what the customer wants, but take the time to check with them as the product unfolds. They are your best source of roadmap input. Use them and reward them for their time. The power of profiling your buyer will pay-off huge dividends for years if done right.


Matt Guruge, CEO, Awato

The importance of understanding a customer’s pain over your solution. It can be hard as you set out working for months on a new product to focus on the root problem you’re trying to solve but your customers don’t care about what you’re building, they care about how it solves their problem.

For us, our first solution was a step in the right direction but it didn’t solve our customers core needs. It took dedicated time, learning and speaking with our customers, to understand what sort of challenges they needed addressed in a product.

It can feel strange to go into customer meetings without the intent on selling them what you’re building, but it can be key to building exactly what they need. Listening; just listening and not selling can make all the difference.


Andrew Rinaldi, co-founder, Defendify

Raising capital to fund the business isn’t something you do on the side or as a brief, short-lived project. As an owner and co-founder, raising money and all the work behind it is part of your full-time job. In fact, it often feels like a second full-time job on top of running the business itself. It can be all-consuming and requires a great deal of time, attention, and effort. Whether you’re working with individual angels, investment groups, or professional VCs, you can’t underplay the volume and volatile nature of work required or importance of investor relations. You have to know this going in and prioritize around it.


Charlie Casey, CEO, Loyalty Lion

If you want to scale your employee headcount whilst maintaining your culture, employ an internal head of people/hiring. Only someone inside your business will understand your values and care about the long term culture of the company.


Amanda Curtis, CEO, N.A.Bld

I wish I had trusted my gut instincts more in the beginning days of the company. Early on it was easy to doubt myself and to look to others who were “more seasoned” for advice. It was right to seek that advice but looking back I should have given myself more credit as I was usually correct in my assumptions.


Jindou Lee, CEO, HappyCo

I wish I knew how difficult it would be to run and grow a company. It’s a very challenging endeavor and often a very lonely one for founders. But I’m very lucky to have a great co-founder and team of people that I work with everyday to overcome each new challenge that we face.


Diane Strutner, CEO, Datazoom

I wish I spent more time learning the art of storytelling. As a founder, you’ll spend most of your time doing it. Storytelling is about setting the stage and delivering the right message to the right audience. It means that although your idea might not evolve, you likely never tell the “who, what, why” the same way twice. I thought that I told a clear story early on, but when I go back and look at old pitch decks I regret not investing more in telling a better story.


Matt Fornataro, CEO, Kompany39

It’s hard to pin point just one thing I wish I knew before I started. My advice would be this: know your worth. Early on you will be told ‘NO’ a lot. It can be deflating. It can lead to doubt and fear and worry to creep in. Especially in negotiations early on, if it doesn’t feel right take the time you need to make an objective decision. Starting out can feel like you ‘have’ to take any deal that comes along, this isn’t true. Be patient, trust your gut.

Another thing I wish I knew was that in the business world, things take time. There are windows / seasons to everything and you need to learn to ride that wave. Everything takes longer and is way harder than you think it will be. If you approach things knowing this, the lumps and hurdles will be easier to overcome.


James Avery, CEO, Adzerk

It can be tempting to try and hire people who you can direct. You might be an awesome engineer, so you hire less experienced engineers. You might be great at sales, so you hire junior sales people because you will be able to mentor them. The problem is, you won’t have time. You will be on the road raising, dealing with 100 things you didn’t think about, and those in-experienced people will be running your company. Hire people who are better than you, because they will have more responsibility than you imagine right now.


Heather Margolis, CEO, Spark Your Channel

You know, it would have been convenient to know that we were going to launch 3 weeks before a pandemic totally shut down the economy for a few weeks. The good news is we are the only platform allowing channel partners, channel sales, and channel account managers to leverage video. The use of video has increased 400% in the midst of quarantine.


Rohit Gupta, CEO, Auditoria

“The value of having a formal sales qualification methodology is super important and cannot be understated. You need to know what is the client’s decision criteria, who is the economic buyer, what is their buying process, who is the competition etc.

Otherwise, you are purely guessing as to how the pipeline opportunity is progressing and are blind to issues that crop up in the sales cycle, either at the client, or due to the competition or other issues. So, we made the decision to use MEDDPICC and every opportunity that is presented had to be qualified under MEDDPICC. This article explains MEDDPICC really well. I can’t understate how many times we uncovered issues due to opportunities not passing the MEDDPICC filters and it’s something that I have embraced whole-heartedly ever since.”


Ben Dowling, CEO, IPinfo

One thing I wish I’d been more prepared for is just how many things there are to juggle, and how much mental energy that takes up. I knew it’d be like that at the start, but thought the problem would get easier over time, but in reality I think the problem actually grows – there’s always more to do, more to worry about, and more to juggle! I still haven’t figured out the solution, but using great tools to help keep organized, hiring great people to work with, and making sure you take breaks and time off is all really important!


Adam Coughlin, co-founder, York IE

A company is not made or lost overnight. One week you will feel like Midas – everything you touch turns to gold. The next week everything falls apart. Those dramatic swings can happen daily and that is part of the process. I wish I had known that and how important it is to remain steady. The highs are never quite as high as you think but subsequently the lows aren’t as low either. If you can become passionate and excited about the process of building a business (and everything that goes into that process) and not just the outcome of having a great business, then you’ll learn every day, which will help both you and your company to grow.

Ralph Paul on Twitter
Ralph Paul
Ralph is the Managing Editor at StartUp Mindset. The StartUp Mindset team consists of dedicated individuals and is designed to help new, seasoned, and aspiring entrepreneurs succeed.

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Ralph is the Managing Editor at StartUp Mindset. The StartUp Mindset team consists of dedicated individuals and is designed to help new, seasoned, and aspiring entrepreneurs succeed.

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