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

• Short week – Having Monday off was a nice break, and it made the workweek shorter. I like shorter workweeks, especially in the summer. I suspect a lot of people will be aiming for as many four-day weeks as possible this summer.    
• Summer – June usually kicks off the summer travel and vacation season. I think this year will be especially active, and I’m curious about how business activity will be affected.  
• Finish line – This week was a reminder to keep pushing, especially when I’m in the last leg of something. It’s important to persevere all the way to the finish line.    

Week sixty-two was a short week. It was good and productive even though it feels like more people have a summer-vacation mindset.

I lived the bootstrap life with my company and learned a lot. It has pros and cons that founders should consider when deciding whether it’s the route they want to go. One of the things I regularly encounter is the full-time team taking no salary.

Building a company is hard. It takes a lot of time and effort. Naturally, you want your team to be focused. This usually means you want them to be working full time on your startup. This sounds great in theory, but it often doesn’t work in the real world. If the team is working full time with no salary (i.e., for equity or deferred cash compensation), they still must fund their lifestyle. They need cash. Some people are fortunate enough to have cash reserves, but most don’t want to burn through their savings. What usually happens is that your team starts doing things on the side for cash as they go longer without pay. As people start doing side things, they lose some focus. As they lose focus, things slow down a bit. As things slow down, people get frustrated. You see where this is going.

Bootstrapping is a good path in certain situations. I did it (albeit painfully) and built my company to over $10 million in revenue. I also personally went without pay and couldn’t afford to hire the people I needed for long periods of time. Founders should avoid asking people to work full time without a salary if that’s going to last for a while. It’s usually not sustainable, and talented people with options (including cash) may be less inclined to accept these types of offers.

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I’ve talked with many founders who’ve been ecstatic upon receiving term sheets, and rightfully so. It’s super hard to fundraise. It takes tons of time and founders endure lots of rejection. An offer in hand is a joyous event. But founders should be aware that the deal isn’t done.

All kinds of things can happen after a term sheet is issued. Some of them prevent founders from receiving the funds outlined in the term sheet. I know founders who have had term sheets rescinded because of world events outside their control.

After issuing a term sheet, investors need to complete other steps before they send funds. The exact process varies by investor and sometimes by deal. It’s important for founders to always have a clear understanding of what steps are left in the investor’s process and what the approximate timeline to completion looks like. If they don’t, they should ask. They should also understand that deals can be fluid—things can be added to the process or removed from it. There’s nothing wrong with founders making status inquiries throughout the process. In fact, I’d recommend it. Most investors will readily share this info.

Founders must understand that Murphy’s law is a real thing. (Remember? Anything that can go wrong, will go wrong.) It can manifest at any time. If the unexpected happens, don’t panic. Be proactive about resolving any issues with all parties involved and make sure everyone is aligned on the remaining steps and timeline to close.

Receiving a term sheet is exciting, but it’s important for founders to stay focused and understand that the deal isn’t done until the money is in the bank.

Successful founders embody a variety of traits. The exact combination differs because every person has unique strengths and weaknesses, but certain traits are more common in successful founders than in the general population, I think. Street smarts is an important one.

When I think about street smarts, I think of navigating bad situations with lots of uncertainty. Often without relevant experience. The term doesn’t mean the founder comes from the streets or was raised in a rough environment. All founders will encounter situations that feel impossible. (It’s only a matter of time.) Navigating them is a key to survival and ultimate success. Founders with street smarts understand when they or their team members are under attack and know how to put up a defense. They also can detect when people are lying or trying to take advantage of them.

A company may not survive if its founder doesn’t have street smarts. If you’re a founder or want to be one, ask yourself: how well do I handle bad situations?

I hope everyone had a safe and healthy Memorial Day with loved ones!

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Today I thought about spring 2021 vs. spring 2020. What a stark difference. A year ago, we faced a massive amount of uncertainty and were deep in a once-in-a-century pandemic. The world stood still for a while, something that had been unthinkable. We’re not in the clear yet, but we’ve come a long way.

The last year is a macro example of how quickly things can change. The world was thrown a blistering curveball that felt unhittable to many. We had more questions than answers. Things looked bleak. But we’ve navigated a lot of that uncertainty and we’re generally in a better place than we were a year ago.

Founders will face tons of challenges on their journey, but they should remember that their current reality isn’t necessarily a predictor of their future. Things can change for the better very quickly. Next time you’re in a tough spot, just remember that in a few months or a year, things could have taken a 180 turn. Hang in there.

Over the past few months, I’ve spoken with two entrepreneurs working on interesting ideas. They’re in totally different spaces, they’re doing different things, and they don’t know each other, but they’re thinking along the same lines. Both have identified a huge pool of people who apply for something but are rejected. Think applicants for loans, school admission, jobs, etc. Most institutions don’t take any further action with respect to the people they’ve rejected.

Both founders think that applicants who were rejected, but just barely, represent a big opportunity. They were near-miss rejections. These people were motivated enough to take the time to apply, which shows a strong desire. The problem is they often don’t know specifically why they were rejected and what they need to do to get approved. These founders are betting that if the reason for the rejection is clearly explained and the additional steps required to get approved articulated, these applicants can be approved.

Instead of lenders, schools, employers, etc. spending tons of money and energy attracting new applicants, they could nurture the near misses, which would probably have a higher return on investment and close rate. Or that’s the assumption.

Both founders are bright and passionate about their respective spaces. I think they’re on to something that could be big. I can’t wait to see how they progress and what kind of feedback they get from consumers.

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

• Opportunity – When an opportunity presents itself, someone who recognizes it and takes advantage of it can change the trajectory of their life. Sometimes it’s strategic. Sometimes it’s being in the right place at the right time.  
• Holiday weekend – I’m looking forward to the three-day weekend. An extra day can make a world of difference.
• Travel – Lots of conversations about travel this week. People are excited about traveling again.    

Week sixty-one felt like a short week even though it wasn’t. I think lots of people were in holiday mode well before the weekend. It felt like a productive but calm week, which was nice.

I had a great conversation with a serial entrepreneur today. He was telling me about a new company and said something that stuck with me. Checkout has been mastered, but the pre-checkout process (i.e., finding what you want to buy) isn’t ideal and could be significantly improved.

The more I think about it, the more I think this founder is correct. There are lots of opportunities to improve how people find items to purchase. Taken a step further, as societal norms continue to change, shopping will have to keep up with them. What consumers are accustomed to socially will influence how they want to shop. There will be many ways to improve shopping.

Commerce is something I’ve always found fascinating and continue to learn about. I’m curious to watch how great entrepreneurs improve the shopping experience!

Today I had the pleasure of giving feedback to a few founders during an office hours session. The format for these varies by sponsoring organization. I’ve most often seen each session lasting ten or fifteen minutes. The founder pitches for half the time and then the investors ask questions and provide feedback. You won’t walk out of these sessions with new investors. But you will likely walk away with some great perspectives on your business and maybe plans for a follow-up conversation.

I like these office hours for a variety of reasons. First, they’re often open to the public—just sign up and pitch, no warm introduction needed. Second, they’re a great opportunity to get quick feedback and perspectives on your business. The investor feedback isn’t super in-depth given the brevity of the meeting, but it can still be very insightful. Third, they’re time-efficient for everyone. Founders don’t spend time networking or trying to figure out how to get a meeting. They just spend a few minutes answering questions and fifteen minutes in the session. Thirty minutes total isn’t bad considering the feedback they get and the possibility of a follow-up meeting.

Office hours are a great opportunity for founders, even if they’re not seeking capital. I encourage founders to take advantage of them. Firms like Outlander Labs hold them regularly, as do accelerators and other organizations. If you haven’t attended office hours, give it a shot.