POSTS FROM 

March 2022

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Weekly Reflection: Week One Hundred Two

Today marks the end of my one-hundred-second week of working from home (mostly). Here are my takeaways from week one hundred two:

  • In person – I attended a few in-person meetings this week. People are full of energy and excitement. I think this spring will be high energy and high activity. We will likely see a lot of pent-up demand released.  
  • Behind – I wanted to complete some priority things this week. I was productive, but I didn’t get everything on my to-do list done. Things are busier than I expected—but I’ve got to get more stuff done.

Week one hundred two was busy, but I was disappointed I didn’t move the needle as much as I’d planned. Looking forward to next week.

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Be Unapologetic about Asking for Opportunities

Today I had a great chat with founder friends about being unapologetic about asking for opportunities, even if the requests are somewhat outlandish. If someone is going somewhere you want to be, ask if you can join them. If someone is working on a project you want to learn about, ask if you can work on it too. If someone knows a person you’d like to meet, ask if they’ll give you an intro.

Some people might call it being pushy or overstepping. I disagree. I think it’s the sign of a hustler. Hustlers get opportunities others don’t. One of many reasons for this is that they ask when others won’t. Of course, you should be respectful in how you ask. But I don’t see anything wrong with making the ask. The worst that could happen is they’ll say no. In fact, people will say no most of the time, and that’s OK. But the one time someone says yes, it could change your trajectory. Sometimes it’s as simple as they like the fact that you asked when others didn’t—they like the hustle and reward you with an unexpected yes.

As one friend put it, “The answer is no to 100% of the questions you never ask.”

Hearing no doesn’t really bother me. When I was an early founder, I was aggressive about asking for opportunities because I had to be. Over the years, I’ve lost a little of that edge. Today was a reminder that I need to get it back and be unapologetic about asking for opportunities.

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Founder Splits Don’t Have to Be Messy

I recently listened to two founders announce that they’re going their separate ways. They shared the news with me over a video call. They explained what each of them plans to do next and why they’re splitting. When they talked with each other about their long-term visions, they realized they’re headed in different directions. So they decided to “divorce” now, before their disconnect causes big problems. The split is amicable.

Building a company from the ground up is hard. Founders put so much of themselves into it that the company becomes their baby. When you have to separate from it, it can be hard and emotional. But founder splits don’t have to be horrible experiences.

If you’re looking for a cofounder but you’re worried about it not working out, or you’re considering splitting from your current cofounder, remember that friendly splits are possible.

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How a Pitch That Bombed Led to a Pivot

I enjoy hearing how founders became aware of the problem their start-up is solving. Sometimes it’s a shower moment. Other times, it’s an aha moment while they’re working on something else. A founder recently shared his story, and it was something I hadn’t heard before. While he was pitching a product, he realized the audience wasn’t feeling it. Translation: the pitch was bombing. He stopped mid pitch. He acknowledged that his pitch wasn’t resonating with the audience. He asked them to share their most pressing problem in exchange for ending the meeting early (i.e., giving the audience some time back). The VP shared a problem the founder had never considered. His team did some research, realized it’s a huge problem, and pivoted.

I love how this founder didn’t force his product on perspective customers. Instead, he read his audience and made the most of the meeting by asking the right question and listening with an open mind.

Good things eventually happen when founders listen to their customers. It can be hard. Founders want everyone to love the solution they spent countless hours building, but sometimes the love just isn’t there. The mindset has to be that what you want most is a successful company—the beating heart of which is solving the customer’s true problem (not the one you wanted to solve). If your solution isn’t resonating with customers, that’s OK. Consider taking more time to listen to their problem.

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Regional Start-up Events Are Back

I caught up with an investor recently, and the topic of schedules came up. We were discussing events we’ve attended and plan to attend. We agree that events are a good way for investors to meet new founders and other investors and learn about new trends. Both of us are looking forward to larger, more regional events, most of which require travel.

I think 2022 will be a great year for in-person start-up events, especially regional ones. There’s pent-up demand for in-person interaction in the start-up community, and I think it will be unleashed this year.

I’m a fan of the hybrid model for events because it allows people to attend who otherwise couldn’t, but I’m looking forward to attending—in person—some regional events this year!

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Add More Value to Win Over Incumbents

I spent today working on a project on my to-do list. I’ve got most of it figured out, but I noticed that one thing is holding me up. The companies I’ve historically used are charging rates that are within the range I’m comfortable paying, but the value of the services they offer has diminished. Translation . . . the cost far exceeds the value, so I haven’t pulled the trigger.

The companies I looked at are likely pricing based on market conditions, which makes sense given the mature state of their companies. But their services haven’t evolved as consumer tastes have changed. Their services don’t measure up anymore. I think these incumbents are unwittingly giving upstart competitors an opportunity to steal their loyal customers. When value exceeds cost, the purchase decision is easier. When cost exceeds value, the result is hesitation—hesitation that can cause a customer to look at others and even give them a try if they like the value-vs.-cost alignment. If the upstart does a good job, they’ve likely stolen a customer from the incumbent.

I decided to keep looking. I found a start-up that offers services more aligned with my expectations at a price similar to that of incumbents. I’m excited to give them a shot and hope they deliver. If they do, I’ll continue using them.

If you’re a start-up going against incumbents, you don’t have to compete by being cheaper. Consider finding areas where they haven’t kept up with customer expectations and then doing a better job in those areas. If you can offer more value than incumbents, you’ll increase your chances of their customers giving you a shot.

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Share Knowledge to Attract Customers

I started working on a project today. I have zero experience in the space and had no idea where to start, so I did some research online. I found a service provider whose site answered all my questions and then some. It had videos and document templates and offered a quarterly masterclass to answer questions. After digesting some of this content, I understood what it would take to complete the project and decided it’s best to hire someone instead of doing it all myself. I decided to hire the company whose content was so helpful. In fact, I didn’t even consider anyone else.

I really like how this company is giving knowledge away, free of charge, to attract customers. No salesperson or email campaign tried to convert me to a customer. Just a self-serve educational process that reinforced to me that this company is credible and trustworthy but also positioned me to complete the project on my own if I chose to do so. I’ll sign up and likely have to talk to a salesperson to become a paying customer, but the salesperson will basically be processing my order instead of having to sell me. Actually, I’ll be pushing them to get me onboarded quickly so I can complete my project quickly.

If you’re an early founder who understands a problem and space deeply, consider sharing that knowledge broadly. It could be a great way to attract qualified customers and shorten your sales cycle.

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Weekly Reflection: Week One Hundred One

Today marks the end of my one-hundred-first week of working from home (mostly). Here are my takeaways from week one hundred one:

  • Perspectives – I love getting different perspectives on things I’m thinking about. I always learn something or am made aware of something I hadn’t considered. This week, other people’s perspectives were helpful.
  • First quarter – We’ve got fewer than thirty days left in Q1. The year is flying by. I want to make the most of the rest of the quarter.
  • Forest – This week, I spent time thinking about things from a higher level and talking them over with others. It was refreshing. It reminded me that it’s important to stop from time to time and make sure I can still see the forest for the trees.  

Week one hundred one was busy and productive. Looking forward to next week.

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What Should I Be Doing If I Don’t Have Product–Market Fit?

I talked to two early founders today who asked questions related to similar challenges. With many things they could be working on, they’re not sure what they should be doing right now. Both have early versions of their products but no product–market fit.

We discussed the objective of this early stage of the entrepreneurial journey: building something that solves a problem well enough that people want to pay for it. That’s always the objective when you don’t have product–market fit. These founders have good products, but they’re missing something. They don’t yet know what that something is. If they figure it out and build it, they’ll find product–market fit and be ready to scale the company around this solution.

When I think about this stage, I see it as a cycle. Talking to customers, distilling what you’re hearing, improving the product based on that feedback, and finding out if customers like the new product are key. Anything that doesn’t support this cycle, important though it may be, probably can wait.

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Intentional Communication Is the Key to Hybrid Work Working

I caught up with a founder friend today, and one of the things we talked about was hybrid work. His team is coming to the office a few days a week and working from home the rest of the time. He mentioned the importance of being more intentional about communication in the absence of physical proximity.

He shared that clear written communication has become more important. When you can’t pop by someone’s office, you likely send a Slack message, email, text, etc. These can be misinterpreted more easily, so it’s important to be precise when you compose them.

He mentioned that increasing the cadence of communication is important as well. Making sure everyone is aligned is always important. Absent daily in-person interaction, some people feel siloed or unsure what’s going on in the company. Sending updates more often and reiterating objectives helps keep everyone aligned. Things like weekly or every-other-week emails from leadership are good at maintaining alignment.

Having run a company that had in-person and remote team members, I agree with his observations. A lot of communication happens informally when people are together in one location every day. Keeping the team moving in the right direction and everyone feeling included is possible in a remote or hybrid environment, though—it just requires more intentionality.

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