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Can I Run Service and Software Businesses Simultaneously?

I had a chat with an early-stage founder trying to figure out his next move. He built a service business to help small businesses. From his work with his clients, he realized that software could create massive value for his service business and other similar businesses. So, he built software and funded that effort with the cash flow from his service business. The beta of the software is now complete, and he sees a large opportunity for it.

This founder is in a spot that feels tough to him. He’s trying to figure out how to continue running the service business and at the same time grow the software business. The financial runway he gets from the service business is important now, absent other alternatives. It pays his personal expenses in addition to funding the software development.

I’ve seen other founder friends with a similar predicament. One specific case comes to mind. My friend’s solution was to hire someone full-time who was his intellectual equal. Both were strategic and self-starting, had an owner’s mindset, and could manage people. My friend put in place an incentive plan that created alignment and transitioned the service business over to the new person. My friend focused exclusively on the software business and never looked back. The software business has become a massive success and changed his life.

If my friend had tried to focus on both companies, the software company would never have become what it is today. He recognized which opportunity had the biggest upside and turned his attention to it instead of splitting his time and mental energy.

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LPs Backing Out on Funds

Over the last few months, I’ve talked with several VC fund managers who’ve experienced fundraising from limited partners taking longer than planned. These aren’t emerging managers. They’ve established themselves with previous funds that returned capital to their limited partners. But as the public market and other asset prices have come down, limited partners have been slower to commit to making new investments.

Today I heard another story: limited partners who’ve signed paperwork and committed to investing in a VC fund reneging. They will no longer provide any capital to the VC fund. Notably, these limited partners are individuals, not large institutions.

This is just one story from one fund manager. I imagine it’s the exception rather than the norm, but it’s something I plan to watch closely. If this starts happening more often, emerging managers and the founders they back will likely be hit hardest.

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Finding Talent Early: A Rewarding Opportunity

This past week, I had independent conversations with a few people about spotting talented people early. Their perspectives varied because they’re in different industries: music, technology, and sports. All three are industries where talented people can have outsize success.

I won’t dive into the conversations, but let me just say they had a common thread: identifying talent before there’s data, traction, or association with a credible brand is hard. For example, Justin Bieber put out YouTube videos before his career got off the ground. Recognizing his talent among a sea of YouTube videos was hard, but Scooter Braun did just that.

Identifying talented people and developing them is arduous work. Many avoid it because it’s so hard. Instead, they prefer to come in after the talent has traction or numbers that are undeniable. There’s nothing wrong with this as it mitigates risk, but it’s not my preferred approach. My view is that yes, it’s difficult, but it’s fulfilling and an opportunity to have an impact. Recognizing something special in someone and helping them reach their potential is incredibly rewarding to me. Especially if they wouldn’t otherwise have gotten an opportunity.

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The Founder Journey Captured in Video: Idea to Exit

The founder’s journey is something the average person can’t relate to. It’s a roller coaster of high highs and low lows. It’s hard to describe, and if you don’t see it firsthand, you don’t really understand it.

Today I found a video that documents the journey of a founding team from the idea stage to the sale of their company. These two cofounders weren’t even sure what problem they wanted to solve at first. The video details their year-long process to identify the problem they want to solve, their fundraising and hiring, and a host of other things. I don’t know these founders or their story, but the video appears to do a good job of documenting their five-year journey.

If you’ve ever wondered what the founder journey might look like, consider watching this video.

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Desperation As a Superpower?

I shared an unconventional view with a friend this week: I believe that desperation can be a superpower when it’s harnessed—and great founders know how to harness it. When people’s backs are against the wall, miracles can happen. But only if their energy is focused.

Why? I think it’s simple: focus. When you’re in a tough or painful situation and desperate to get out, you zero in on what’s important. You ignore everything else. You focus on the things that can get you out of the situation. You’re not thinking about what you’ll do after or what you did before. You’re locked into the current situation and trying to escape it.

Nobody wants to be in a desperate situation, but life happens. If it happens to you, don’t give up. Some of the most unlikely outcomes—outcomes we celebrate—arose from the ashes of a desperate situation because someone focused and refused to give up.

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Know Your Metrics to Stand Out

Today I had the privilege of attending an event where two early-stage founders pitched the cofounders of Tiger Global and partners from Bessemer Venture Partners, Charles River Ventures, and Alsop Louie Partners. The founders did a fantastic job. I was curious to hear what feedback they received—it’s not often you’re able to hear feedback from such accomplished investors regarding early-stage companies.

The comment that stood out most was about metrics. The investors were impressed by both pitches, but the founder who included detailed company metrics was phenomenal. Customer acquisition cost, lifetime value, gross margins, projected revenue, and a host of other metrics were included in her pitch. She spoke confidently and demonstrated that she had a great handle on the levers that matter most and that drive her business. The panel said it was rare to see an early-stage founder have such a great grasp on the metrics of their business so early. They praised her and asked her if they could follow up with her so they could learn more.

If you’re an early-stage founder with a product in the market, identify the metrics that matter most in your business and focus on moving them in the right direction. Understanding these metrics will help you both stand out at this stage and make better decisions.

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The “Forward Intro Email”

I was communicating with Roy Bahat by email. I ended up asking him for an introduction to another person. Roy, who is great, quickly agreed, asking that I send him a “forward intro email”. I reviewed his format and loved it. I’m often asked to make email intros, and I agree with what Roy says in his post. Anyone wanting an email intro should consider using Roy’s format. It will make it easier for your contact to make the intro, which will likely lead to the intro being made faster.

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Your Loved Ones Might Not Like Your Becoming a Founder

I recently listened to a founder’s wife share her reaction to learning that her husband wanted to quit his lucrative job and start a company. She was angry, and understandably so. Life had recently dealt them a series of positive and negative jolts, and this would be another jolt, albeit self-inflicted. They discussed the decision ad nauseam. Ultimately, she decided to have faith and support her husband in pursuing his dream. It’s early in the company’s journey, but things have gone well so far, and she’s happy that she supported him.

Becoming a founder isn’t a decision to take lightly. People don’t discuss this as much as they should: starting a company probably will greatly affect the founder’s loved ones. Start-ups don’t have many resources, so the financial impact can be hard for a family to adjust to. Especially if the financial load is now on one person. Just as important is time. Early-stage founders put tons of time into their start-ups, which leaves less time for loved ones.

If you’re thinking about starting a company, be sure to consider and consult your close loved ones as you’re evaluating entrepreneurship. You and your team will be under an inordinate amount of stress to make the company succeed. It will be much harder if you’re under similar stress at home. In a perfect world, you want your loved ones to be your main cheerleaders and supports. They’ll find it hard to live up to that if they haven’t been included in the decision-making process.

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New Networks = New Ideas

I shared some views on the importance of networks with someone recently, including how being part of different networks helped me navigate my early founder journey.

One thing I didn’t realize back then was that being part of diverse networks was valuable because it exposed me to new ideas. I learned about all sorts of things I would have never known about. Some of those ideas became transformational for me, altering my trajectory. Exposure to new ideas is something I now seek out, because it helps elevate my awareness about the world and my thinking in general.

If you want exposure to new ideas, consider joining different networks.  

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A Burn-the-Ships Mentality

I listened to an investor and founder give his thoughts on what it takes to win and how he identifies winners. He described how he evaluated one of his most profitable investments: Uber. When he invested in the company early, he was betting on the founder, Travis Kalanick. Travis was intense and had what this investor calls a “burn-the-ships” mentality.

During wartime, when ships arrived at an enemy’s shore, the generals instructed the troops to burn their own ships once everyone had disembarked. The only way the troops would go home, they were told, was by taking the enemy’s ships. There was no turning back—winning was the only option.

I’d never heard an investor describe a founder in this way before, so it stuck with me. I’m all about backing founders who have a drive to win, but I’m not sure that a “burn-the-ships” mentality is a necessary or even good thing. I don’t know enough about Travis or the early Uber story to talk about them. I do believe, though, that there are ways to motivate your team to win without burning the ships.

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