Top Startup Advice & Lessons from Interviewing 12 B2B Founders

Episode 13 – Season One: Founder's Journey Roundup
Transparent sales process - working together
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It’s hard to believe we’re already finished with season one of the From Vendorship to Partnership podcast! 

Throughout the season, I talked to 12 startup founders & leaders about their experiences: the highs and lows of launching a company, finding product-market fit, signing their first customers, and building their teams. As a first time founder myself, I look up to all of these leaders, and talking to them was helpful – and a lot of fun!

Looking back on the season, I was impressed at how candid each founder was willing to be. They didn’t shy away from the challenges, mistakes, and all the tough moments that come with building a company. In hindsight, this makes sense – you have to be humble and willing to learn from your mistakes to continue growing.

The goal of this podcast is to dig up valuable, real startup & sales insights in a short amount of time, and I’m grateful to all of the guests for being willing to get real!

Two common themes I noticed across the founder interviews:

  • Be customer-obsessed. The founders shared a passion for deeply understanding the problems they were trying to solve and the people they were trying to help.
  • Be people-obsessed. From deciding on key hires in the early days to developing their company’s culture, many founders said that building a strong team and relationships made a huge difference in their startup’s success.

In this week’s episode, we’re changing things up a bit. Accord co-founder & CPO (and my brother) Ryan interviews me about my key takeaways from Season One: Founder’s Journey.

Listen on Apple Podcasts, Spotify, or wherever you get your podcasts, and keep reading for a roundup of lessons & advice from all of the founders we talked to.

💪 Finding product market fit

Reprise logo

1. Sell the idea, then sell the product.

“Sell where you want the product to go and see if you can bring people on your journey. Then actually put your product in front of people. Does it change the way they do their job so that they need it, and it’s not just a nice-to-have? That’s the test of product-market fit.”

- Bryan Stevenson, CEO & Co-Founder, Reprise

Scratchpad logo

2. Obsess over user adoption.

“Since Scratchpad solves for multiple types of users, instead of finding product market fit first, we went for product-user fit: ensuring that users loved our product enough to actually use it regularly. We knew that the majority of sales tools that exist fail because they just aren’t adopted, so we obsessed over that.”

- Pouyan Salehi, CEO & Co-Founder, Scratchpad

Mosaic logo

3. Build a solution you would want to use.

“We knew that if we built the product we would want to use and would solve our problems, it would resonate with our customers. Our investors called it ‘founder-market fit.’”

- Joe Garafalo, COO & Co-Founder, Mosaic

ZenHub logo

4. Don’t take product market fit for granted.

“Product market fit is an ever changing, ever evolving thing. You can have it one day, but then the market changes and it might be different, or gone.”

- Tyler Gaffney, CEO, ZenHub

👯 Signing the first 10 customers

Atrium logo

1. Validate your problem, get feedback, and the rest will follow.

“The first thing you need to do is validate that people actually have this problem and do a lot of great discovery calls. Ideally, then you can put together a customer advisory panel. If your product solves their problem and fits the market, then it all kind of just folds together.”

- Pete Kazanjy, Founder, Atrium & Modern Sales

Cocoon logo

2. Make a hypothesis about who your early customers will be, then test it. 

“We had a hypothesis that our early adopters would be high-growth tech companies, because people are their most valuable asset. Then we tapped a LinkedIn community that was known to try new HR tech, and started reaching out to everyone we knew at those companies.”

- Lauren Dai, COO & Co-Founder, Cocoon

Remote logo

3. Set yourself apart from others in the market.

“We said, ‘We’re going to do this differently. We’re going to be very transparent about pricing and allow people to sign up on a waitlist.’ Once we were ready to launch, thousands of companies were already on the waiting list, and we chose the ones that were the best fit.”

- Job van der Voort, CEO & Co-Founder, Remote

Sendoso logo

4. Understand the difference between early partners and your first “real” customers.

“In Sendoso’s very early days, we had 30 or 40 customers, but they weren’t ‘real’ customers. They were friends and family, or people that we as founders were selling to. I think you can find product market fit in the early founder sales. But if you really want GTM fit, then you need to have non-founders selling to strangers at a price point that scales.”

- Kris Rudeegraap, CEO & Co-Founder, Sendoso

🛠 Launching a product & building a team

Pocus logo

1. Focus and prioritize your efforts – don’t try to do everything.

“There’s a lot we could be building. Your gut reaction is that you want to build what you think is cool and fun. But you need to build what your customers need now.”

- Alexa Grabell, CEO & Co-Founder, Pocus

Metadata logo

2. Launch early, even if you don’t feel ready.

“You should build something that you’re kind of embarrassed about and immediately try to sell it. See what people like, what they don’t like, where their jaw drops – and use that as your feedback loop on the product.”

- Gil Allouche, Founder, Metadata

Assemble logo

3. Know your strengths and hire for your weaknesses.

“Enrique and I were deep on a lot of things related to GTM. So early on, it was more about how to build a strong engineering team, so we could spend more time than the average founder doing GTM-related work.”

- Lisa Wallace, Co-Founder, Assemble

Balance logo

4. Build a strong relationship with your co-founders.

“With some relationships, it can feel like 1+1 = ½. With others, it feels like 1+1 = 5, and that’s where I am with my co-founder, Yoni. It’s amazing how effective that is.”

- Bar Geron, Co-Founder, Balance

💭 Advice to other founders

“Keep asking the tough questions. I think we get too complacent because startups are exhausting. You’ve got to be asking basic questions all the time.”

- Tyler Gaffney, CEO, ZenHub

“Find amazing co-founders. There’s no reason to do this alone.”

- Lauren Dai, COO & Co-Founder, Cocoon

“Be okay with being uncomfortable. When you start a company, the highs are going to be high, and the lows are going to be low. And put things in perspective – the problems we’re having right now we only dreamed about having six months ago.”

- Joe Garafalo, COO & Co-Founder, Mosaic

“Don’t take everything so seriously. Obviously, Pocus is my baby. But at the same time, I want to be enjoying the journey and not just the milestones.”

- Alexa Grabell, CEO & Co-Founder, Pocus