Work smarter and harder.

As a startup founder, there is a strange dynamic that success brings. Success means that you are now adding resources but likely working even more hours. If your startup isn’t doing well, there isn’t much to do. For what I call “civilians”, these are people that you meet at dinner parties and find out that you are an entrepreneur and say “you are so lucky to be your own boss and set your own hours.” My response is usually something that sounds like, “yeah, I choose to work all the hours”. It turns out that sarcasm is under appreciated and according to my Instagram feed is the sign that I’m a genius. If anyone tells you to “work smarter, not harder” they are possibly in a large established corporation or in academic research.

How does the evolving role of the work change for a founder? Here is your ultimate playbook, that you will not follow. In fact, if my family reads this, they will probably tell me to take my own advice.

First let’s talk about the category of tasks at hand. The founders single job is to take the business and turn it into a great story that people can both easily understand and repeat to others. Then it’s about adapting the story to a myriad of audiences and get the message out. Whether it’s to investors, customers or potential employees…that’s the job.

Here is the playbook, as always I’m biased towards founders in
the built environment, say construction tech and PropTech. Let’s just say the KPTech market. All the things that I focus and invest in.

There are 3 categories of target audiences for your message.
1. Nearterm
2. Midterm
3. Strategic (also Long Term.

Nearterm- This is the audience that will/can affect weekly, monthly and quarterly results. The results that it can effect are sales, revenue, hiring plans, and generally working capital. As a founder, in the early days you will build your strategy and likely do most of the tactical tasks yourself. As the business grows, you will still own strategy and likely writing content (NEVER outsource this) and others will help with the tactical. Formatting, loading into a system, etc but you still own the strategy of delivering relevant content to the relevant audience. Based on sales cycles in the KPTech industry, I doubt this is top of the funnel but likely an audience that has been aware of you for 6 months or longer (yes and uggh). CTA (Call to Action) is pretty direct at this point and about converting all the previous activities to results.

Midterm- This is the audience that will/can affect monthly and quarterly results. And will likely impact the Nearterm results, and additionally impact your balance sheet. How? It takes at least 6 months to raise capital. If you do it faster than that, there is a high likelihood that you may have the wrong investors. While these activities can drive Nearterm funnel flow, you should also see things that don’t follow a typical funnel flow. What I like to call “blue birds”. I don’t remember where I learned that term, but it’s the results that come out of nowhere. These blue birds change the game. If you haven’t ever experienced a blue bird, then you may be doing it wrong.

Strategic- This is the audience that affects your annual results. The main impact of the results here are your balance sheet and your valuation/exit opportunities. This is all driven by the founder.

Now that we have the categories, this may not be game changing for you. It’s likely just organized a bit of what you already knew.

One of my favorite KP sayings is “A great founder knows the difference between friction and an immovable object.” Too many founders expend resources on immovable objects and run out of them. Let me explain a bit on how this is relevant to the above.

Take a look at a calendar and think about ideal times to “release” each of the above activities. Think critically about “when”. Why do I release this newsletter called the Sunday Scaries on Sunday? Part obvious but also, all the best founders work Sundays and actually have time to read. Their work is quiet but their brain is not. Remember those civilians that said you were so lucky to make your own hours? I release it weekly, because the audience can absorb it weekly. I also don’t take holidays off. You will get one this Thanksgiving and Christmas as well. Build your weekly release times and your work blocks to build the content. Guess what? You may not have an audience that absorbs content weekly (I doubt it) but it’s possible. Also, do not get attached to the quality of your weekly content, however be
obsessed with being consistent.
Now that you have looked at the weekly calendar, now look at your monthly calendar. This is likely where your Midterm content will play out. Contemplate what your message is, who your audience is and their ability to absorb. While I may be the hardest working VC in the business (not a brag, just need more hobbies), many VCs take long weekends, the summer and holidays very seriously. If your method is email, you want that email landing when they will actually read it. Not buried under a bunch of emails after Labor Day weekend.
Let’s look at the annual calendar. Take a look at events that you are attending/speaking at, etc. Events don’t “sneak up” on you. If you go to Greenbuild or AU every year, then you know what it is and when it is. I was talking to the CEO of a mega-billion dollar company. It takes almost a year to get on their in-person calendar and is best done if they are already going to be there. You want to meet with the CEO of Autodesk? Start working a plan now and you can build a story that he would want to meet with you at AU next year. The biggest ideas and strategies take a year to happen. Imagine planning now versus trying to get a meeting 2 months before AU. You will expend 10X the resources or more and the probability is low.

Part of my motive for writing this is that I am planning out the rest of my year. A big chunk of this is the holidays. Do you think I’m “taking off” the week of Thanksgiving (only celebrated in the US) or the week of Christmas (they get like 1 day off in India)? I will definitely get some family time, but “off” is probably not happening.

Creating a calendar of how you want to plan out this year and next is the biggest part of working smart. BTW, did you know that this is planning season for most of your customers? This is when you should be talking enterprise deals and budgeting for next year. I asked a client about whether we needed to give them a proposal so that they could budget us for 2025. He said, “you guys are a rounding error in our budget, don’t worry about it” . My internal reaction was “dang, we didn’t ask for enough”.  

I have had a few questions about my incubator this week. Yes, I’m very involved.
No, we don’t invest.
Yes, we charge $500/mo

The reality is that the Seed stage companies that are venture fundable, I just invest in.
The incubator is to help the “too early” and “too late” companies. VC is a Goldilocks thing. Taking an investment from an incubator can be the most expensive money that you will take with varying value and benefits. For those of you that know me, I am possibly the most connected person in the KPTech market. I get asked for introductions and advice all the time. For my portfolio companies, they have already been through a ton of hours of due diligence. They get unfettered access. For incubator companies, I (we) need to get to
know you and understand your fit with our network. Think of it as KPs Cotillion. We need to get you ready for the big opportunities that lie ahead for you. For example- My upcoming 8th annual summit is coming up. We host a Demo and Drinks. Can’t have no scrubs pitching.