My Ménage with a Startup: 10 tips on Protecting Yourself from the wrong Venture

Self Care Sex and Love

Sex and relationships can be far less complicated than the back bending, tantric positions in which you’ll find yourself when trying to launch a successful startup.  Between managing egos, balancing life, and the countless meetings,  the experience can leave you – raw. Add the constant pressure of securing funding, and you’ll feel like you’re on the wrong side of the casting couch. So be prepared, especially if you plan on trading your nights of Netflix and Chill for Caffeine and Code.

My NE heartbreak came just days ago, after a part-time love affair with a small tech boutique, left me blue and no happy ending. My dreams of changing an industry and seeing my name on every mobile phone, gone before I could buy it a second drink.  I poured my heart into it, leaving little reserve for myself, while ignoring the obvious signs of a bad relationship.  I didn’t protect myself and subsequently, I got burned.

Nonetheless, there will certainly be a better-fated, less emotionally driven rebound, but until then, here are a few rules for safe play I should’ve remembered from my last grind session with that “Startup Life”. Hopefully, they’ll help you determine whether you should swipe left.

1.’So, we’re just friends now?’ Hey, don’t get stuck on Titles.

Devoid of the traditional missionary corporate structure, most startups are now flat and agile. The titles are nice, but they represent nothing substantive. “CEO” doesn’t  impress a savvy investor that gets hit on daily. Product, passion, and the drive to succeed do. So unless you’ve got a good route to market, your title’s irrelevant

You see it on Shark Tank, mom and pop shops pull in thousands in investments, sporting nothing more than the bareback title of “the love of my life”, not Chief Officer. It’s about that “Ride or Die” life, not that forced contorted reach around. Too many players get caught missing the actual connection with their customers and partners, while neglecting the dialog with their investors.

The big “O” happens where you find the positive friction of team dynamics. An obsession with titles is about you, not the other person. Working teams go farther than any executive-labelled fictions.  Let the dynamic speak for themselves, keep pushing forward, and decide on titles later.

2. Awkward Moments in Intimacy – is your new reality.

Sucks if you’re an introvert like me, but you’re going to get close (Cooties be damned) so be warned. Late nights, sleep deprivation, and the passion that drives your innovation, will drive you closer. It can forge great long term relationships with the right people, if you’re all in healthy places. My first product launch happened nearly twenty years ago and I’m still friends with some of those colleagues. You learn things about each other that you never wanted to know,  sometimes building a nearly unbreakable bond.

Otherwise, set boundaries or you’ll have that “did they just fart on the first date” look plastered on your face for the duration of the project.  Even worse, if they’re toxic, it’ll poison the project. Lean back, enjoy the ride, and protect yourself.

3. FWB is risky business, in business. 

Navigating a friends with benefits relationship has it’s perks. You’re comfortable, you know each other, an its easy to get to rousing non-committal bliss.  More often than not though, people’s “feels” get in the way, damaging otherwise great friendships. As a result, sometimes you really should be “just friends”.

Building relationships during the startup process is one thing, but bringing in preexisting friendships is risky. Working together with egos, power, big decisions, and money, introduces a new kind of volatility that tests boundaries. If you’re looking at maintaining these relationships beyond flirtation and foreplay, plan a long term exit strategy that leaves you whole. Talk about it and prioritize. Determine what’s most important, the business or the friendship. You may be forced to choose.

5. Poly isn’t for everyone.

You can love one or many in various forms, and they can love you right back – just fine. However, when you treat partners or your startup like a side piece, you’re setting one up for failure.

Part One
: There are tales detailing meteoritic rises of pseudo-part-time business IPOs. That’s the exception. Maintaining your day job, while trying to engage in a startup on the side, is hard work. They’ll both suffer if you don’t balance. If this startup is your passion, it can consume you, taking you away from other relationships, including family. You may have to let something go.

Whereas, if you’ve gotten to the point where your startup is making money, even if its not quite enough, you may consider abandoning your other gig to cultivate that particular passion. Do what’s right for you and don’t feel trapped. It’s hard if you’re dependent on a steady paycheck, but if you’ve got an option for extended paid leave to explore possibilities  – take it.

Part Two: In business you unquestionably need to know how many partners are in play, because it impacts the value of shares and the valuation of the company. I had seven partners of which I knew, amongst countless others the CEO kept courting. The more partners or distributed shares, the less paper for you. As part owner of that relationship, you have a voice. Speak up even if it means walking away.

My situation was a result of a partner gone wild, where regardless of the horrendous implication, the person with the biggest checkbook won. Yes, size matters even in business.

5. ‘where were you last night?’ Expect honesty.

If you happen to find inconsistencies in your partners’ stories, reports, or behaviors, sometimes its predictive of an impending problem.  When you find compounding lies building, even if you try to address them, only to find seemingly pathological denial or avoidance, be forewarned.

If your partner needs to stop every 4 hours for another blue pill, that’s ok. What’s not acceptable is them running to the bathroom instead to text another partner in between your session, then  lying about it to you both. Realize you deserve better. And if its a short term fling for you, be up front. If you’re in for long haul,  IPO or relationship, be honest. Talk about the future, setting real expectations.

6. Testing and Transparency are key.

Know your Status. From bedroom satin to financial ledgers, honest communications about what you can’t see between the sheets can make or break relationships. If you’re in a startup prospecting for funds, your finances are often tested and scrutinized. Your tax returns – fair game. LLC’s give you protection when multiple partners are incorporated, however, if you’re dealing with a single owner as the primary filer, they may hesitate disclosing their financial little black book.

That wouldn’t be the end of the world except, bad investments, questionable spending, judgements, liens, and legal actions all come up during due diligence. Think divorce court and lingerie receipts. If you’re betting on someone’s clean bill of health for your future, they should be willing to share documentation with you. You’re entitled to see balance sheets, budget, P&L, and for lovers, an STD report.

7. Keep those naughty text close. 

Sexy text promising what’s to come, build excitement and can get you off, but sometimes those promises have implications. In business that translates into unethical behavior and legal disputes.

When it comes to payment terms, “get it in writing” is standard. However, what we fail to chronicle is our creative contributions, which help in legal cases, where patents, trademarks, or copyrights are subject to scrutiny and swayable juries.

Startups lend themselves to these kinds of infractions regardless of what you signed.

(Also, get a lawyer to review your docs before you join ESPECIALLY if shares are promised, and if applicable, get them checked BEFORE you leave).

8. Remember how you met? Awe… No, really!

This triviality is more Important than it seems. Picture this: You’re in a room, or on the phone doing an investor pitch and your fiscal inquisitor asks a question so simple, you smile assuming your presenter’s got it handled.

Where’d you meet?”

Simple right? Yet my partner stumbled all over the place trying to come up with something he “thought” would work, when the truth was right there. It was a miss, and whether he was hiding something or not, the appearance of unpreparedness or deception, was introduced. Neither good when you’re requesting near half a million dollars. He played fluffer for the rest of the meeting.

Sure, if you met on a shady online site you’re not comfortable sharing, have a “truthful enough” story at the ready.

We worked together on previous projects on our day jobs, in a very difficult. Then over the last two year we found an opportunity to make something great happen, so we pooled our resources and here were are trying to change an industry.”

Or, in relationships,

“I met my spouse in Round Rock, TX. She wore a black leather coat, it was raining and we were off to the Hairy Man Festival, which we’d not yet know was cancelled due to the unseasonable torrential rains. I drove a white Maxima at the time, with an expired tag, which she noticed right away, but didn’t comment. When I saw her, I knew she was the one, I still remember her smile when I introduced myself and said – Hi. I’m Alix.”

That goes further in selling relationships than, “she was hot and I was horny, so damn I had to have that” or “We’re a team of successful professionals that stumbled across each other, here’s our credentials, give us money.” WTF?

Remember that the dynamics during investor presentations isn’t only about the product or service, its also about you. Ideas build brands that are delivered by people and if an investor makes an emotional connection with you, they will help sell that intangible, or use it for positioning. Its about the dynamic of showing you can deliver. You don’t need all the answers, but your team should be able to demonstrate proficiency in problem solving or at least show a modicum cohesion. Build a team that showcases that.

Hint: Good porn – is well, porn you like. Great porn is still porn you like, but made by people that appear to know how to work together, regardless of the number of participants (no judging).

9. ‘What do you mean I’m just alright?’ manage your value.

Don’t sell yourself short and don’t let your partner belittle your contributions. For some of us, our time is our greatest investment. If I broke down my hours to a pay rate, I’d argue that I invested significantly more than most other partners. And when you take into account ideation, obsessive whiteboard sessions, conversations at all hours of the day/night, and opportunity costs, it was a pretty penny.

However, when your partner continuously brings up your “soft investment” verses his raging hard, nearly purple “financial investment”- it wears on you. Losing money never hurt as much as hearing your contributions devalued or called worthless. You can get the ring back, but never the time.

The words “I never really loved you”, have an unparalleled lasting, and recurring sting. Work with partners that appreciate or at least compensate you well. And if you’re working on the promise of shares for payment or deferred payment, understand that shares of a company that has no valuation, have no value. (That’s rash worthy lesson).

Financially, the ‘hard’ investors get the benefits of losses (taxes), you get uncompensated risks. If you can work on a contract basis, with agreed terms for binding payment (deferred or not), then you at least have a vehicle for recourse later should things go awry. Worse case scenario, you too, can reap the benefit of loss.
Don’t let them treat you like a recurring disposable one-night stand, (unless, of course you want).

10. Excuse bad ideas, but not bad behavior.

Lastly, you can recover from bad ideas, but bad behavior can’t be dismissed.  Choosing a direction, then applying course correction is standard. A prevailing concept in innovation management  is “failing quickly, ” finding out what works, then if it does, do, if it doesn’t, get it out of the way. It shows you’re trying to accelerate something to market. But if you’ve got someone Hell bent on being right, even though all evidence suggest contrary, or when their ego gets in the way, or they consistently lie or change their stories, or they refuse to acknowledge mistakes, or worse, repeat the same ones, while impacting your credibility as a professional – run.

That’s good advice for life, because you may like sex, but no one likes getting “screwed”.

Look, these are eyes wide shut precautionary tips and I don’t want readers to stay clear of startups. If your passion is there – feed it, strike out on your own. Find a way to self fund, angel investors exist. Change the world your way. You can compromise, without being compromised. Its a good time to be out. Female founders are outperforming male-only teams financially by 63%. One out of five startups looking for VC funding has a female co-founder!  And according to the Kaufman index:

In 2015, 41% of first-time, new entrepreneurs were non-white, a growing national trend. In 2016, the majority of entrepreneurs seeking venture will be minorities–either non-white, female, or both.

That’s exciting. So go out there, have fun, but please use protection.

On another note, I now have more time to get back to writing…

– Alix

My Ménage with a Startup: 10 tips on Protecting Yourself from the wrong Venture

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