Four Pieces of Advice for Today's Founders

There are countless ups and downs a new founder goes through while building their company. This is true whether it's your first company or your fifth.

Yin Wu recently sat down with Madison McIlwain and Claudia Laurie, hosts of The Room Podcast, to share some valuable advice learned along her journey as a 3x founder.

The trio discussed strategic advice on subjects like:

• Fostering a culture of ownership
• Making tough calls as a founder
• Building a founding sales team
• Tips for raising in a challenging market

Below, we’ll summarize Yin’s key takeaways. You can check out the full podcast episode on Spotify or Apple Podcasts.

Fostering a culture of ownership

Some startups describe themselves as a “family.”

At Pulley, we consider ourselves much more like a high-performance sports team.

Each of us has a job to do, and we are expected to do it to a high degree. People are held accountable when they don’t meet those expectations. 

Yin shared that a powerful way to get buy-in on this idea is to place a strong emphasis on ownership for your team.

You want employees that are truly engaged. By prioritizing equity and ownership for your team, you’re making sure they’re bought in not only mentally but financially. 

As an early-stage founder, you can’t compete on cash comp alone. Equity is your biggest asset. Get them invested in your company (through equity comp) to lift engagement and connection to work.

Making tough calls as a founder

As a founder, you’ll be faced with no shortage of difficult decisions. 

Yin shared her decision-making process when she’s been in this position in the past:

If you go and talk to people that you respect, and if everyone is saying the same thing, just go and do that thing. But more than likely, with the tough challenges that you face, two people are going to say X, and two people are going to say Y. If that's the case, that means there’s no right answer, and you need to own that decision either way. “

At the end of the day, it's your call as the founder, and sometimes you just have to make it. But a good question to ask yourself here is, “What is the decision that I’ll regret the least?”

One of the hardest decisions a founder may have to make is whether or not to pivot and how to move forward when a pivot is necessary.

Yin’s last company, Double Labs, went through many pivots before eventually settling on the product that was later acquired by Microsoft.

When considering a pivot, Yin gave two great pieces of advice:

1. Choose a market you're passionate about, AND that is growing. The rising tide lifts all boats. If you don't have both, you won't be able to stay focused on helping those users for years to come.
2. Learn to be resilient & adapt to abrupt changes.

“There are so many things on your plate…There’s the TechCrunch perspective of what it's like to be a founder, where it’s like everything's amazing, everything is working. And then there's reality…We all know there is the emotional rollercoaster of being a founder…The part that I didn't understand until I actually went through it is that the emotional rollercoaster can actually be on the hour by hour basis. You think you're on top of the world when you close an amazing deal, and then you get an email literally the next second from a customer saying nothing is working.”

Building a founding sales team

Yin, Madison, and Claudia dove deep into the factors founders need to consider when building a GTM plan and team.

Here are a few pieces of advice Yin had to share:

• Start out with founder-led sales. At the super early stage, buyers are taking more of a shot on you as the founder than on the product. You really need those early customers to help you refine the product. When Pulley was just getting a start, Yin would sit down with other founders, ask about their cap tables, and then help them install Pulley right there on the spot.
• When you hire Account Execs, hire two. That way, if performance doesn't meet expectations, you can establish whether it's the sales rep or the product.
• Use your ACV to determine which channels are viable. For example, if your ACV is on the lower end, an outbound approach might drive your CAC too high to be viable, meaning a low-touch, self-service inbound model might be more appropriate.
• Worry less about what your competitors are doing. You want competitors to exist. If they don’t, it's a sign you’ve gotten into a bad or non-existent market. Concern yourself more with building a solution to a real problem your customers are having.

Tips for raising in a challenging market

The funding environment is tough right now. 

Investors are more conservative and risk-averse than they have been in previous years, which generally means they’ll be looking for greater proof of traction, be more frugal with funding amounts, and seek greater downside protection.

Yin had some great advice to share here:

1. If you get a term sheet, strongly consider it. It's hard out there right now.
2. Raise as little as you need to make it to the next milestone. Smaller funding amounts are easier to raise.
3. Understand what your options are in any funding scenario and what you could be giving up. That’s one thing that Pulley tries to help with by providing founders with tools like the Fundraising Modeler and the Term Sheet Scanner.
4. Don’t over-optimize on valuation. Many founders focus too heavily on this. The startup journey is a long one, not an overnight success story. Look to get the right people (investors) on board who can help you along the way.

Get more first-hand knowledge

Yin’s episode with The Room Podcast is packed with first-hand insights from her founder journey, as well as great advice from hosts Madison and Claudia.

She shares valuable advice for building an innovative team culture, making tough calls, and raising in the current funding environment.

If you want to check out the entire podcast for a full exploration of the above points, you can find it on Spotify or Apple Podcasts.

Plus, be sure to follow Yin on Twitter to learn more about foundership, equity, cap tables, and growth.