Venture Capital – Page 18 – Julie Fredrickson

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.

Creativity is scary. Any time you build something new fear lurks around the corner. Because even if it’s not rational, your perception of risk rises when your potential for failure is at its highest. Perhaps this is why when you take a conscious risk you unconsciously try to mitigate any unnecessary additional risks. This has a number of significant consequences for businesses. You want to feel safer when you take risks so you seek out psychological safety from your associates. The principle is simple. You will only take risks if you believe you don’t be punished for it. Psychological safety has been shown to be crucial for teamwork.

I’d wager this is a factor in why startup teams tend to be homogeneous as human nature makes it harder to trust what we don’t know well. Which is fascinating when you consider that diversity is also an important factor in financial performance. And as much as this principle of psychological safety been discussed for team performance, there is one area in startup land where feeling safe is rarely cultivated: venture capital.

Venture’s entire culture is steeped in cliches of competition and combativeness. Which seems odd for a group that theoretically prizes high performance. Wouldn’t they benefit from cultivating psychological safety the most? 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. And surely plenty of ink has been spilled on picking good partners in the literature of startup advice. And yet the atmosphere of distrust is pervasive. Venture capitalist and entrepreneur are constantly managing the information flow between each other. Which is exactly the opposite of what creates the necessary safety to take creative risk. So why isn’t this discussed more?

Imagine a fund who instead of poking holes in your data or lobbing grenades in your plans instead showed it was sensitive to the parade of fear and doubt that pervades most decisions. You’d get more done by a mile. Ideas could be refined instead of defended. Plans could be buttressed and shored up rather than rationalized. Having safety will lower the kind of inhibiting social pressures to show “that you are always crushing it” perhaps enough to produce startups that actually do go on to crush it.

This strategy could shift the dynamics of a firm’s competitiveness too. In group dynamics of status and posturing prioritize deal flow among only in group group members which disadvantages everyone by increasing competitive deals and rising prices. Funds who who have psychological safe founder relations will then disproportionately control what deals get done as the creative risk takers will seek them out. That kind of deal flow would be a major leverage point. Rather than getting stuck fighting for the same deals everyone agrees on (which isn’t a sign of quality no matter how much we want it to be so) venture fund that sticks to prioritizing psychological safety will spend more time with productive risk taking that builds the future.

Developing emotional capacity isn’t a platitude. It’s grueling work that takes place over years, sometimes to little effect given our innate resistance to change. But it is truly transformative.