This week, I’ve been thinking about incremental progress, forgiveness, and eating healthier.

Questions

Business

How do I ensure success as we kick off our first pilots?

Nayak.ai has launched our first pilots, with Scrumlaunch and Claratti.

Scrumlaunch is testing whether following a talk track will improve outcomes, and Claratti is testing whether it’s possible to achieve similar results with less technical salespeople as more technical salespeople.

As we kick off our pilots, success is top of mind. Here are a few ways I’m giving us the best chance at success:

1. Handhold to ensure usage.

   One pilot hasn’t had that many sales calls lately! And the one seller we had onboarded hasn’t had any. So I needed to reach out to the buyer and see where the problem was. It turns out the seller we’d onboarded hasn’t had any calls scheduled — so we need to onboard another one who does. We have a call scheduled for Monday to do that.

2. Hold the kickoff call.

   The buyer at one pilot has rescheduled our kickoff call. It’s December, it’s the holidays, there are always excuses. But we can’t succeed if we don’t kickoff. So my goal this week is to make sure we actually hold the kickoff call.

3. Set expectations upfront.

   The first two points were about logistics, which are important. But we need to make sure that once they use Nayak and get onboarded and kickoff that they love it. To me, that means setting the right expectations upfront. We have success criteria defined, which is always critical in sales. What I’m talking about is expectations around the platform. We are still early stage, so there will be bugs. We don’t have an admin panel yet. We need to be sure they’re not expecting the world and disappointed with what we deliver — that means in the kickoff calls and onboarding calls being upfront and honest about what we can do now, what we plan to do soon, and what won’t be possible for awhile.

This is my favorite part of running the startup — talking to customers and seeing their reactions to using it. I’m excited by our progress so far.

Personal

What advice do you have for founders in navigating romantic relationships?

I wrote a longer piece about this on Medium where I get into more of my complete thoughts around this (and I have a lot). If you’re interested in learning about the founder’s mindset, how it differs from the nonfounder’s mindset, and what that has to do with relationships, I encourage you to read the longer piece.

The short version is: It takes honest communication, healthy boundaries, and realistic expectations to build a healthy relationship at the same time you’re building a company.

The medium version is:

Honest Communication

Anything short of total honesty can breed resentment. An honest conversation around starting a company while you’re in a relationship is almost impossible if you don’t know what you’re getting into. So first, consider deeply what you’re getting into — long periods with zero income, working a day job and building your company, exhaustion, money trouble, and stress.

I can pinpoint the moment my relationship was doomed. I needed to take out a loan, and I asked her if she was OK with it. She said she was. I wasn’t being totally honest, and she neither was she. I had left out some details — minimum payments, how it would affect our finances. And she was probably comfortable with the idea of me taking out a loan, but as soon as it became concrete and actual, she was not comfortable with it.

Healthy Boundaries

Set rigid boundaries around work/life balance. You might want to take every Sunday off work, pick a night every week you end your day at 5pm and don’t do any work after that. It can be easy to become a workaholic as a founder. There is literally always more to do. You need to set some boundaries around when you’re working/when you’re not or else you always will be. Use these periods to give your partner quality time. Close your laptop and be present.

And set boundaries the other way, too. You might want to set a boundary that you need to focus between 9-5 because you’ll be deep in the work. Don’t be a dick about it, but setting explicit boundaries around when you’re in deep work will be healthy for your relationship too.

Set Expectations

I regret bringing my partner to Tulsa for Techstars. I needed to ‘disappear for awhile,’ to make the startup my number one priority for those three months. I was the only one of the 15 founders in the program who brought their partner with them.

Another founder said, “This is a bootcamp. We’re here to build.” And having my partner with me split my obligations in two contradictory directions.

As a founder, you will need to disappear for periods of time. Set the expectation, communicate clearly, and make sure both your needs are being met. In a healthy relationship, your partner should also communicate their expectations of you. “You can go to Tulsa for 3 months, but I want to talk every day.” Or “I want to make plans to see each other.”

It’s Not for Everyone

The startup life is full of uncertainty, pain, and discomfort. You put in long hours, money, sweat, tears, and you lose sleep, and you might still fail!

That’s not a life everyone is OK with.

Just because something is good doesn’t mean it won’t end. And just because something ends doesn’t mean it wasn’t good.

Misc.

How can I eat healthier?

This week, I’m trying to keep it simple and easy. I’m paying attention to how many processed, preserved, and fresh foods I eat.

I believe not all calories are created equal; fresh fruits, vegetables, and meats are better for you; processed foods are more likely to be unhealthy.

And it’s impossible to track what you don’t measure, so I created a Google Form to track how much processed (candy, chips, sauces) unprocessed (fresh fruits, vegetables, and meats), and semi-processed (canned food, frozen food) I’m eating.

Here’s a sample of my results from this week:

My observations:

• It’s really hard to track something I do as frequently as eat in something like a Google Form (but the habit is building).

• The measurements might be skewed because I don’t track amounts — just whether it’s processed, unprocessed, or semi-processed. I wasn’t sure whether to count every fruit or chip as a separate entry or do something else.

• Because I don’t track amounts, it might have incentivized some bad behavior — well, I’m already going to track this single chip as processed food, so I might as well have a handful.

• It still feels useful to keep track of these things, even if this specific method might be flawed.

I don’t know if I’ll keep this up, but it’s been an interesting exercise for this week.

Quote

Reflection

I’ve been tired this week. Very tired. It feels like I’ve been going for a long time without a break.

I’m excited to take some time off around the holidays.

It can be hard to take time off as a founder, and I’m grateful to have the chance to take a break soon.

Qs for Next Week's Newsletter

Business

How do we prioritize which features to add to the product next?

Personal

How can I make the best use of my time off around the holidays?

Misc.

While I’m back home living with my parents, how can I have a social life even though I don’t live very close to my friends?