Interesting Meeting #1: “But can you ask someone for money?”


Last week, I had the pleasure of meeting with an investor and entrepreneurial advisor who took an interest in both my current role at the consumer neuroscience company and in my [personal] side projects.

We talked about the side project, the side-side project, and the top-secret side-side-side project, which makes for a total of n=5 people knowing that one even exists!

It was only after we had been chatting for an hour that he very seriously asked,

“but, are you capable of asking someone for money?”

I didn’t respond at first because I didn’t understand the question. Was he asking if I, literally, had the capability to do so? (Yes. Doesn’t everyone?) Was he asking for some reference point where I had already asked someone for money? (see: Shark Tank audition 2012.) Was there some sort of evidence that I could provide that would support that I could, in fact, ask investors for money or did he just need to know that I had the moxie to do it? (Talk is cheap.)

He continued and said, “I’ve seen many (wannabe) entrepreneurs walk into an investor meeting, pitch them, and end the pitch with ‘ok, thanks for your time, see you later and please contact me if you have any questions’ and I want to know that you can actually close the deal.”

I decided that the right strategy would be share with him that not only could ask (and had asked, and closed) investors for money in the past, but that I had a process for doing so.

My first step is to determine if the investor is more interested in investing in the person (me) or the idea (the product). One particular challenge I’ve run into is that my on-paper background doesn’t outright support that I can bring a project to execution and see it through. I have a failed company under my belt, and a propensity to find the shortest feedback loop possible in determining if something is the right fit for me (see: big pharma). I have been incredibly successful in figuring out what I don’t want to be doing and how to exit from it as gracefully as I can. If the investor I’m speaking with is a “people-guy” then I spend a non-trivial amount of time addressing the questions he has about me, my background, and my previous accomplishments/failings and have to curtail my frustrations towards him not wanting to hear about my ‘brilliant’ idea and the plan to make it happen. If he’s an “idea-guy,” I’ll discuss not just the idea in incredible detail, but the process to execute it. ([x]Idea * [y]Execution = $! where x and y are how good your idea and execution of said idea are). I’ll get as granular as he needs me to get and rarely at the end of these meetings do I hear anything like “well, what makes you think you can do this?” because the thoughtfulness and thoroughness behind my strategy is exactly why I think I can do this.

I can determine what kind of investor I’m speaking with based on the types of questions he is asking. A guy who says he’s interested in getting to “know you as a person” but only asking about pre-market valuation, marketing strategy, and exit plan is an idea guy. The guy who stops you mid-sentence and says that he “needs to understand why you’re doing what you’re doing” is likely to fall in the people-guy category. Keeping a running mental tally of the questions he’s asking helps me figure it out. This matters in helping pull the right levers throughout the conversation.

My second step is determining whether or not the investor I’m speaking with is a fast-twitch or slow-twitch decision-maker. In other words, what’s the potential latency from introduction > meeting > pitch > deal. Telling the fast- v. slow-twitch decision makers apart comes from paying attention to how quickly (literally) they speak, how often are they interrupting you to get information faster, how rapid-fire their questions are. When you talk to a fast-twitch decision-maker (guilty, by the way), they’re likely running through a series of checkpoints in their head and trying to download the information necessary to address those checkpoints as quickly as possible. They’re detail-oriented but have little tolerance for a low signal-to-noise ratio. Efficiency is key, even at the risk of some packet loss. The slow-twitch guys tend to “feel” less intense and allow for some meandering of your answers, don’t interrupt as much, don’t speak at 100-mile-a-minute and might even say things like “I’m going to need some time to think about this” or “I’m not in a rush to invest” etc. They too have a checklist of questions you need to answer, but have more tolerance for granularity. This matters because different types of decision-makers are likely to be optimal investors through different stages of your company (seed v. Series A) and understanding what kind of decision-maker you’re dealing with helps set your own internal expectations.

Finally, and most important, there’s the big ask. At the end of the meeting, I will (almost) always end with,

“Are you interested in investing?”

By the way, unlike Shark Tank where you stand up and ask for an investment of x dollars for y% of the business (immediately signaling toward your perception of your company’s valuation), I don’t really care about the details of the deal at this point – how much money or equity and what kind doesn’t matter here (yet). I’m just trying to figure out if this guy is going to invest.

If he says no, then I ask for some constructive feedback and if they’re okay with me reaching out to them at some future date with an update. (This is in line with my “burn no bridges” mentality.)

If they say yes then my next question is, “how much are you interested in investing?” If they come back with anything other than a discrete, fungible number, (a range, pushback, needing to discuss with someone else) I ask, “is there any additional information I can provide for you that will lead to you providing me with that number right now?” If the answer is yes and I have that information available to me, I provide it. If the answer is no or more pushback, I see it as a signal that they’ve decided not to invest and loop back to the “thank you for your time, I’d love to know if I can reach out to you with an update in [x] days/months.”

This is my process. I’d love to hear your thoughts. Tell me everything.

The Things They Carried, Literally

Women’s purses are scary. One of my favourite activities is to ask a man to hold my bag while I’m doing something (tying my shoe) and enjoying how awkward they look. Another one is to permit someone to go into my purse to get the gum/charger/whatever they asked me for. Sometimes, they just end up bringing the whole thing to me rather than trying to get the item themselves. Women’s purses are also interesting; I am actually quite fascinated by the one-page spreads some magazines do where they ask a well-known woman to share the contents of her purse. I see a lot of business types (Sandberg, eg) carrying things like notebooks and pens while the model-types will carry a lot of makeup.

As I was getting ready for yet another trip (leaving for SFO on Sunday morning), I became acutely aware of how heavy my purse has become in the last few weeks. As a woman who never actually used to carry a bag, in the last few months I’ve had to adjust to carrying [most of the] things I need with me at all times because I’m always running from one meeting/city to another. I’m pretty good about cleaning out the extra stuff I put in it throughout the day but was curious as to why it still felt so full, so I emptied it out to see its guts.

Aside from insatiable curiosity, imperviousness to guilt, and my iPhone (not pictured, because I needed it to take the picture), here are the things I carry every day.
inthebagIn arbitrary order:

  • Kindle Paperwhite: I read a lot of books. Under it are 3 magazine articles a good friend saved for me (since May!) because he knew I’d enjoy reading them.
  • Clif Bar: I always have one of these on me because I like food.
  • Business cards: They’re pretty cute. I designed them myself. I’ve not yet given one out!
  • Mophie juice pack/charging cable: I go through 2-3 iPhone battery cycles a day.
  • Headphones: I used to carry earbuds but I have tiny ears and they always bugged me after awhile. These help me get some quiet time wherever I need it.
  • Water bottle: I have a theory that I’m perpetually dehydrated and I’m trying to address it by carrying a full water bottle around with me at the start of each day. By drinking the water, I lighten my purse. Win-win!
  • Lucas’ Papaw Ointment (the little red tube): I bought this because it claimed to cure all sorts of ailments (bug bites, scratches, burns) and as I’m constantly injuring myself — today I discovered a bruise on my thigh that I can’t quite remember happening — I’ve gone through 2 of these in the last 6 months.
  • Wallet: when I was younger[er], my father and I started this tradition where he would give me his old Mont Blanc leather wallet after he felt it had worn out. I was 12 or 13 the first time I inherited his hand-me-down wallet and I remember that it smelled like a mix of his cologne, cigars, and old leather. (All 3 remain some of my favourite smells.) Last year, after the 3rd (or 4th?) hand-me-down wallet he had given me was too beat-up to continue using, he surprised me by mailing a sort-of brand new one. He’d purchased it, sprayed his cologne on it, and worn it around for a few weeks before sending it. This also explains why I never used to carry a purse; men’s wallets fit in pockets!
  • Baby wipes: Have we met? If yes, then you know how clumsy I am. I spill things on myself constantly and these help mitigate damage.
  • Gum: Because you never know when you’re going to have your face really close to someone else’s face? I feel like this one’s super obvious!
  • Band-Aids: confession: I pick at one of my fingers (middle finger, right hand) when I get stressed out. Now I carry band-aids to protect myself from well, myself.
  • Lipsticks: I actually carry no other “touchup” makeup with me, which is surprising given that I cry my mascara off with tears (of laughter) at least once a day. Or, I’ll wear no makeup. But in the case of needing to feel slightly polished, a swipe of lipstick does the trick.
  • Sunglasses: I’ve been on a Ray-Ban avs kick for the last few months.
  • Nerd glasses: I’m blind. Sometimes my contact lenses hurt. A lot.
  • Moleskine notebook x2: iPhone notebook apps are great but there’s nothing that quite replicates the tactile piece of physically jotting your thoughts down. The little notebook is full of random thoughts, doodles, and coffee stains. The bigger one is an agenda type that I use to plan out my week.
  • Passports (in green cover): dual-citizenship means two passports and a cover helps keep them together. Since I spend a lot of time in airports, I like to give myself the option of taking the quick flight to visit my fam in Montreal, or a mini-getaway to Mexico.
  • Pens: see Moleskine notebook x2
  • Minions Happy-Meal toy: A few years ago, when the Minions made their first appearance in Despicable Me, I fell in love with them because they made me laugh hysterically. My best friends and I saw Despicable Me 2 as my 27th birthday “party” (I know, I’m so cool…) Since then, I’ve been gifted with Minions hats, cakes, t-shirts, USB keys, and friends incorporate the little guys into everyday text-message exchanges. This $1 toy also makes ridiculous sounds and will make me laugh in pretty much any circumstance, no matter how stressed I am. It takes up very little real-estate for how much happiness it brings me.
  • Hair-taming accessories: My hair is always somewhat out of control and when it reaches critical mass, I at least have a headband, bobby pins, and hair ties to tame the beast.
  • Post-its: I love the collection of sticky notes by Knock Knock and usually have one of their cheeky pads on me at all times. The joke started when I worked at an all-male company and would jokingly stick the sticky notes on them as a signal that they’d violated an HR rule (inappropriate comment, dirty joke, etc.).
  • Charm bracelet from one of my best pals: A friend of mine ordered a cheap charm bracelet from some nerd website and it had a brain, a microscope, a neuron, and a dopamine molecule on it. He also gave me the little rocket ship from his “physics” charm set (I’m obsessed with all things fast) and between this and the little Minion, I have some physical/tangible items that remind me of the people I love.)
  • Keys: I have 5 sets of keys to apartments in 3 different cities. Only one of those apartments belongs to me. I have some pretty fantastic friends to entrust me with the privilege (and responsibility) of unlimited access to their homes.