Tag: Founders

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Finance Startups

Day 149 and Optimizing for Outcome

I came across a thread today by Sahil Bloom on human goal setting and the mental models we manipulate. He introduced me to Goodhart’s Law

When a measure becomes a target, it ceases to be a good measure. If a measure of performance becomes a stated goal, humans tend to optimize for it, regardless of any associated consequences. The measure loses its value as a measure! Goodhart’s Law is states “Any observed statistical regularity will tend to collapse once pressure is placed upon it for control purposes.” But the concept was popularized by anthropologist Marilyn Strathern. She generalized the thinking and called it Goodhart’s Law. “When a measure becomes a target, it ceases to be a good measure.”

I am fascinated by this tendency humans have of fixating on the things we think symbolize progress instead of the actual outcome. Sahil names a number of instances in which this has led to bad business outcomes. CEOs managing to short-term stock goals has been one that has long frustrated me.

Startup land is immune from this tendency either. I’ve seen product teams fixate on OKRs such that they never miss a single metric but fail to launch their product on time. Or a venture capitalist will toss out something like an ARR goal for a Series A only to have a founder chase that number for a year and still not get funded when they hit it. We think these goals are the goals in and of themselves. But really launching the product on time and closing the series A are the only thing that matters. As long as we hit our goals who cares what metrics we used?

This is of course set against the classic “what gets measured get managed” which is an apocryphal quote from business theorist Peter Drucker. It may in fact be total bullshit. It may be that measurement actually hinders management. Said rather well by Simon Caulkin

Measures set up incentives that drive people’s behaviour. And woe to the organisation when that behaviour is at odds with its purpose.

Lest you worry this is just a business problem when I was single in my twenties I made a spreadsheet of the various gentlemen I was dating. I felt like I needed a way to make the process more efficient so I starting weighting categories of characteristics that was most important to me. I like intelligent men so I started listing their college degrees. I liked men who were into quantitative thinking so I started noting if they worked in banking or academics. And well you can imagine how this took a turn for the worst. Instead of meeting smart men that likes to look at the world through numbers I met a lot of bankers that went to Harvard. I was optimizing for the wrong outcome.

Next time someone tells you that some metrics or goal is the only thing that matters stop and question if it makes sense for the long term objectives. I’m not saying bankers from Harvard aren’t smart but I’m also not saying that all smart men are bankers from Harvard. And that turns out to be a pretty crucial difference.

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Categories
Finance Startups

Day 146 and Gossip

Gossip drive the world. The stories we tell about other people reflect a lot. Even if we claim we don’t care what others think what others think moves the world around us. And I would posit that this actually isn’t a bad thing. It can drive closer bonds and increased connection.

There is a concept in evolutionary psychology called indirect reciprocity. Natural selection favors strategies that base the decision to help on the reputation of the recipient. Social interactions in which one actor helps another and is then benefited by a third party are key to cooperative reputations.

This isn’t just a systemic population level issue either. People who are more helpful are more likely to receive help. It’s uneven obviously and people can obscure their reputation. Depending on if you are up or downstream of helping or being helped, you make different calculations. Some people help more but they feel it’s worth the cost. They are downstream. Others accept more help because they are upstream. We are all making trades based on our position and arguably they are fair market trades.

How we decide to cooperate and with whom is driven considerably by reputations and shared value beliefs. Relaying reputation signals to bolster your capacity to connect to others is actually a key part of empathy. We need to establish psychological safety to partner with each other. Gossip helps us find suitable relationships. This is especially true in disciplines which require creativity. Quoting myself on the topic of psychological safety in venture capital.

If entrepreneurs are solving entirely new problems with high chances of failure feeling like they can trust their financial partners should be a top priority. Yet the atmosphere of distrust is pervasive. Venture capitalist and entrepreneur are constantly managing the information flow between each other.

Managing the information flow is a key component of gossip. Showing you understand their context, their fears and their reputations concerns helps you. An act we denigrate in popular culture actually helps you to deepen the relationships as each signifier breaks down space between two people and builds trust. So don’t knock gossip. It has evolutionary, societal and individual benefit. Just remember the ultimate outcome is about bringing people closer.

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Startups

Day 125 and Working With Startups

One of the most frustrating aspects of startup life is the vendor startup relationship. There are so many pitfalls and disasters that can befall each side. That naturally leads to a lot of dysfunctions as each optimizes for their own needs, a process that unwittingly leads to the disasters we sought to avoid in the first place by trying to prevent issues.

From a startup’s perspective there are two key issues. Established businesses tend to be slow moving. They are slow moving as they have process and documentation. Nothing is more frustrating to a startup than needing a nimble partner that can throw shit at the wall only to get a meticulous vendor that documents all the shit that didn’t work in exacting detail. This isn’t to say that one shouldn’t report (in a remote first culture documentation is even more crucial) but 40 page decks on what happened will send a founder running.

From a vendor perspective startups are frustrating because they never have any of the assets, documentation or processes in place that make your job possible. Anyone who has become embroiled in a mess of half functional SaaS operation software knows what I mean. How are you supposed to deliver on a contract when all the basics you need from a startup are impossible to locate and occasionally contradictory?

The tension between the two workflows is clear. Especially because startups eventually become more process driven and operationalized over time and vendors are always looking for ways to become more nimble and cost efficient. So you’ve got two parties who want to become more like the other, but as they do that risks upsetting the partner that chose them for the opposite virtues. If this were a romantic relationship it would be heading for a breakup. “You’ve changed man!”

My best advice to vendors is to be as flexible as possible with startup clients. The faster you provide an output the more likely it is that the founder will come to rely on you. Most successful startup vendors simply roll up their sleeves and start producing. They don’t scope in too much detail or negotiate contracts that lock them in, no, successful startup vendors know they give themselves security and contract stability simply by giving a founder what they need every day. As you find more needs you act on it. You stay flexible till suddenly you’ve become the crucial partner that gets budget every quarter. As a startup grows becoming the indispensable partner means that you grow along with it. Your goal should be to have your client succeed at the same pace that you are succeeding.

My best advice to founders is to allow your vendors best traits to rub off on you. Paying attention to their competencies allows you to build up teams that support that. That then enables your vendors to perform even better for you as the fluency on expertise develops. Great marketing teams don’t just produce great marketing in-house but rather they allow it to flourish in the entire ecosystem. There is a reason why CMOs have winning agencies and winning agencies have great brands. The truth is that you will always get the most out of your vendors if you respect what they excel at and spend your time and money prioritizing that support.

The danger if you don’t make productive vendor startup relationships is two fold. One startups will waste valuable capital with a partner that was never a good fit. Two vendors will waste billable hours and employee energy on accounts that have a high probability of imploding. It’s a waste of money for both sides. But when it works well lol it’s absolutely money.

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Finance Startups

Day 96 and Founders Who Don’t Want to Be CEO

My Twitter has been going viral with reply guy friendly topics like taxing high earners and public vaccine demand so I needed to get some niche startup content in today to clear my palette of the reply guys. So I’m going to think about founders, professional management teams and venture’s role in supporting founders. You know, a topic that won’t have strong feelings.

A non zero number of my founder. friends would probably pay to be extracted from certain stages of startup growth, especially later stage scaling, but somehow being founder friendly has come to mean keeping these founders in charge all the way through. Many excellent zero to one founders have to actively change their entire style, skill set and value proposition once they get a company past about employee 25. Obviously there are many inflection points in startup growth and many founders relish the opportunity for constant skill growth. But plenty of early stage founders hate stuff like Human Resources and operations. Shit a good chunk hate sales and marketing too.

Early stage work is a speciality. It’s a professional niche and hard to train folks for as it’s part personality and part dysfunction. I think we should value early stage founding for its disproportionate impact on value creation instead of forcing these early stage specialists to train to become generalists, great managers or scaling operators. Of course it’s more likely they will fail once you take them away from the stage where they are genius.

Recently a friend of mine who works in venture said of another investor “oh that VC is old school” and clarified it meant they like to bring in executive teams for their B rounds companies. Which honestly sounds like a dream to me. There has to be a middle ground between firing visionary but scattered founders once they’ve raised and trying to coach a mediocre manager into great growth CEO.

I think we should normalize founders being churned in on new ideas rapidly and churned out on scaling quickly. Let them get back to founding. Let them create more faster. Great scaling venture funds can provide more value by bringing in a scaling leadership team and easing the founder out to areas where they can focus on vision and direction. I say let the professionals run your team.

Obviously some founders dream of going from idea all the way to IPO but I don’t know if it’s the dominant path they desire. It could just be one of many. I have very little interest personally in shit like operations, process and scaling. I literally married a COO rather get good at it (insert joke about literally anything to avoid therapy). However it shakes out the “founder friendly” venture firm will remain. What it means to be founder friendly may need to be rethought.

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Chronicle Startups

Day 53 & The Process

Startup land can feel exclusionary and clique driven. Looking in from the outside it can seem as if all the power and money is concentrated into a few groups that only fund and hire their friends. Less charitably it looks like a circle jerk.

While this isn’t an incorrect perception, I believe why we think it is exclusionary is very different from the reality of why it is exclusionary.

Startups are tight knit because successful companies have high psychological safety. We all tend to work together again and again and back each other’s plays because we have built up a high trust environment in order to survive. Even if we don’t exactly see the vision someone else has we trust that they will find a way to make it into a reality.

We don’t trust that this is true for everyone. Ideas are like assholes in that everyone has got one. It’s the ability to turn a formless expanse of ideas and hopes into a company that makes a product it’s customers like. It’s extremely hard to make something new. Harder than you can ever imagine if you haven’t tried it. So people who make a living out of making something from nothing have developed a set of heuristics that let us determine if someone outside our circle is capable of making “a thing” to prove their ideas can become reality.

We tend to overweight people that build tangible things. Even though many of the most crucial skills in business are the less quantifiable ones. We tend to overweight people that have demonstrated any kind of success in zero-to-one work even if what they want to build isn’t remotely related to what was done in the past. This is how despite most of my experience being in advertising tech and e-commerce I was backed to make cosmetics. People had faith that I could flip the bit from off to on.

While this may make it seem hopeless if you are currently not inside the system that’s not what I hope you take away. Startup people love watching newbies make the leap. I cannot overstate the fondness we have for someone gathering up the courage to spring into the unknown. I used to hate the phrase “I’m rooting for you” till I realized everyone actually did want me to succeed. They just rightly realized I needed to learn the hard lessons in my own time. They could give me all the advice in the world (and believe me they did) and sometimes I just needed to make the mistake in order to learn the lesson. The mistakes allowed me to succeed.

Of course, we always hope people will learn from our advice and not require the pain of a fucked up cap table or a growth plan that missed target because we burned our cash position down to three months runway. But most people that are genuinely good at startup work appreciate that only the person actually “doing it” can make the choices that lead to success.

So startup folks will always be excited to give back and encourage those that want to try “doing it” too. If I have a clear ask I find I get an answer from even the most successful and prestigious. Literally CEOs and world famous developers of entire languages will just email you back. It’s honestly miraculous. I have invested in cold emails. Championed them to my nearest and dearest. Because we believe that the process of making something from thing doesn’t exclude anyone. You just have to show someone that you will try to make your vision a reality.

Categories
Chronicle Finance Startups

Day 51 & Unwritten Rules of Startups

I’ve been shifting my working attention towards angel investing. As I talk with more founders, particularly those sent to me by my venture capitalist friends, I’m noticing how much bad advice is circulating in the discourse.

There has been a consistent trend of thought pieces and generalist advice in startup land that gets published by those that find attention helpful to their careers but don’t actually want the risk of sharing the unvarnished truth. Think TechCrunch thesis pieces and founder medium pieces. I’m guilty of engaging in it to a significant degree.

But it’s getting to the point where I feel bad that I’m not doing more to correct some of the bad advice or “true but not in your case” advice. It’s persistent and chronic and doing significant harm to certain communities of founders particularly those that are underrepresented. If you are a founder please DM me on Twitter or email me Julie dot Fredrickson at Gmail for further dish.

Founders regularly get terrible advice on fundraising metrics. Lower your CAC with blending channels (don’t please be honest about cost), you need to show faster growth so increase spend (growth is good but can kill you dead), organic growth is more appealing than marketing spend (it depends organic is hard to replicate and scales unevenly) and my personal favorite stack your MoM growth charts it looks sexier (so does a push-up bra but eventually you get seen naked).

Another area that gets weird is how much bad advice there is in fundraising process. You get told to drive FOMO and excitement but no one tells you just how much investors talk. Founders inadvertently tell white lies that are so transparent it’s the source of constant back channeling. There are so many cliques and power structures you don’t appreciate till you are more entrenched. Startup land lives for it’s petty feuds and rivalries. Be careful trying to play funds off each other as it’s rare for anyone to be fully blacklisted (though it happens) and you don’t know how close to partners may be or if they hate each other’s guts. Some folks look nicey-nice on Twitter but fucking loathe each other in reality. We’ve got cliques for female founders, gay founders, Christian founders, libertarians, fitness freaks, data geeks, retail hounds, SaaS sluts, and yes some of these are just fun to say. Be careful with back channels. You never know who may actually be crucial to your deal or a significant power player. Or who vouching for you can turn an entire deal around. Many of the most respected startup folks don’t maintain social media presence at all. So don’t be rude if you can’t judge how important someone is from their bio. They might tank your deal or get you tracked to a partner who writes a term sheet.

Be carful about optimizing your raise for specific outcomes like valuation or time. I know fundraising sucks but it’s also your job. You will have to do it again and it gets harder each round. You go with a higher valuation and you have to grow into that number. Are you sure you raised enough to hit the metrics? If not you get recapped next round. That only hurts your ownership and the VCs don’t really care. Are you trying to get it done fast so you can move on with your life? Lol guess what now you are stuck with that board member for a decade or till your startup dies. And a bad board can kill you dead. Or make you wish you were. The chances of you slowly sinking because your board has a toxic relationship with you is much bigger than the chance that you will grow so fast you always hit your metrics.

A big part of startup life is accepting that your ego does you more harm than good. This life will humble you. And generally everyone just wants founders to succeed. We want to help you avoid the mistakes we made. But not everything will apply to you. So don’t take every bit of advice or you will constantly be at the mercy of others. Context matters a lot.

But you must learn to listen and adjust your course or you may end up chasing metrics that don’t matter with a board you hate and a valuation that you can’t life grow into.