Life lessons from karaoke

Today is international women’s day, and though it’s not earth day, I’m going to recycle/reuse/re-purpose some content from a talk I had the pleasure of delivering to a group of high school girls one year ago in honor of this very day. Here’s the Cliff’s notes version.

The early years
orchestraAs a young girl, I was painfully socially awkward.  A nerd before geeky was chic. Couldn’t get a date to save my life. My brother still reminds me my best friend was the library. Oddly enough though, I didn’t suffer from stage fright; I grew up in school plays, orchestra concerts and even a performing dance group in college (so, so much lycra). I was hiding in plain sight, behind other people’s words, music and choreography. I told myself it wasn’t really me on that stage.

fitting inRight after college, I got recruited into a management development program at an industrial supply distribution company. I knew more about logistics and socket head cap screws than anyone should, and was given an unbelievable amount of responsiblity. At 22, I lived in fear of being discovered. I was managing people (mostly men) who had been doing their jobs for as long as I had been alive, so I started wearing heels to be tall enough to look my direct reports in the eye. Less consciously, I started adopting the management style and speech patterns of the (mostly) men around me. I didn’t even sound like me; I just wanted to blend in.

Karaoke changed my life
bush gardenJust over 10 years ago, I moved back to my native Seattle. Being Jewish on Christmas Eve, my brother and I went Bush Gardens: the temple of karaoke, 365 days a year. As we walked in, (my now uncle) Bob Santos was belting out Ave Maria in Latin. It was magical. I realized that no one in that bar cared who you were outside of that moment. On or off stage, you check your day job, your ego, and your baggage at the door and become part of this communal experience. I was hooked.

Karaoke lesson one: Get over yourself. The people  who love you will love you no matter what. Those who don’t know you probably don’t care. With that in mind, it really takes the pressure off of “failure,” whether it’s a disastrous song selection or a career change.

On my early path of karaoke discovery, I had a career revelation. Coincidence? I think not! I had just about had it with corporate life, and realized that what got me out of bed in the morning wasn’t my day job but my volunteer community activities. Life is too short for that. I got over my corporate identify and lifestyle, quit my job and decided to go back to school full time to pursue my dream of running a nonprofit organization.

Karaoke lesson two: Find yourself. My good friend Ericka Lee, a serious karaoke queen, throws the gauntlet every time we go out: you have to “skaraoke” (aka, try a brand new song) at least once, as that’s the only way to expand your repertoire.

I’ve kissed a lot of frogs to find that prince of a song. Along the way I learned to sing what’s in my range, not what I wanted to hear. I love dancing to ABBA, but have no business singing Dancing Queen. With many skaraokes under my belt, I’ve found my songs: Adele and Aretha Franklin.queen of soul

My career “skaraoke” was in grad school– my pal Andy Boyer knew I was bound and determined to go into nonprofit management, but recruited me onto a team for a venture capital investment competition. Serendipity is a beautiful thing (as is a nudge from a friend); in life I generally have a plan but am willing to change it in favor of a better one, and thus entered the wonderful world of entrepreneurship. I’ve never made less money nor have I ever been happier. Supporting startups is most definitely my song.

Karaoke lesson three: Be yourself. I am not, nor will I ever be, the Queen of Soul, embodied by the fabulous Ms. Franklin. So when I sing “Never Loved a Man,” it’s inspired by Aretha, infused with some Angeline Ball, but at the end of the day it’s all me. So no one can say I’m a terrible Aretha. I just try to be my best Rebecca.

sinatraTwenty years after starting that first management job, today I wear heels by choice.  And because you can’t do a post on karaoke without the Chairman…

Forget blending.  Find your song and sing it, your way.


The Art of the Coffee (Meeting)

The Art of the Coffee Meeting

9 Tips for mentees, mentors, and yentas

As a genetically pre-disposed yenta, over the last decade I’ve managed to find myself work that enables me to do what I love: be a matchmaker and a coach. The great news is I’m far from alone; our community has a powerful peer-to-peer mentorship movement afoot.

Kyle Kesterson, who is, in fact, a Freak'n Genius.

Kyle Kesterson, who is, in fact, a Freak’n Genius.

Luminaries in the startup community, including Marcelo Calbucci and Kyle Kesterson, hold regular entrepreneur office hours. Seeking mentorship can be a great forcing function– you’ll have to crystallize your thinking on what you and your business need. Providing mentorship is a great way to stay on top of your A-game–there’s no better way to truly understand a topic than to have to explain it. As a community we can help each other with introductions (matchmaking) and learn from each other’s mistakes (coaching). So how do you unleash the power of the mentor network if you’re just getting started? Here are some first-date tips:

For “Mentees”:

  • Ask for advice, not help. Everyone likes to feel like an expert. Not to mention, desperation is a stinky cologne (thank you, Super Troopers). Listen well, but don’t forget, it’s your company (thank you, Techstars). That means seeking advice is a poll, not a vote: the decisions are on you.
  • Make it easy to say yes. Put guardrails around the request: “I’d like to meet for 30 minutes to get feedback on my investor pitch deck.” That meeting has a good plot: a well-defined beginning, middle, and end.
  • Respect the network. Remember whoever introduced you to this new connection is putting their reputation on the line for you. Therefore:
    • don’t embarrass them: I’m not talking about chewing with your mouth open– though maybe don’t do that either– but do show up prepared and ready to take notes.luke and yoda
    • close the loop and let them know if the intro was helpful; they’ll be more likely to do it again. From where I’m sitting, Joey Kotkins of Inside Social (Techstars class of 2013) has achieved jedi master status in this arena: timely, brief, informative follow-up. Part art, part science, but at the end of the day, all discipline.

For Mentors:

  • Respect the request. Just because someone asks you for advice, if she doesn’t take it, it doesn’t mean she’s a bad “mentee,”  or even a bad listener. She can consider your opinion without agreeing. Better yet, to avoid this trap, try not telling entrepreneurs what to do, but instead ask them probing questions. Comparing notes with investor and mentor Kim Rachmeler, she’s fine-tuned the Socratic method for startups, an approach that truly enables entrepreneurs to own their destinies.
  • Protect your network. If my mental rolodex is doing my bidding and we’ve had a good meeting, before I finish that non-fat latte, I’ll try to mention a few comparable companies or potentially helpful connections. Instead of rushing home to do those intro’s, however, I really do want to know if they’re the right resources, and will ask you to circle back and let me know if they are.  And yes, it’s a test. If you don’t take the time to check them out, it doesn’t bode well for how you’ll treat those connections in the future.
  • Beware calendar creep. Carve out a set time, every week or every month, whatever the frequency, so it doesn’t take over your calendar. Don’t nickel-and-dime yourself with the commute time to and from meetings, so pick a place, stay put, and pack as many meetings as you can into your allotted time.  These days, mine is Thursday afternoons at Ada’s Technical Books and Cafe.

Everyone can be the good kind of yenta

  • Ask for permission, not forgiveness. Call me old-fashioned, but 9 times out of 10, I’ll seek a green light before making a requested connection. If they’re up for the connect, giving them a heads-up can get you faster, better results. If not, better you (than your connection) get the redirect/no/non-response.

    Help me, help you

    Help me, help you

  • Life is too short for hidden agendas. Start with the end in mind: “a good meeting will result in [___________].” Once you figure that out, let your coffee date in on your game plan. Call me Jerry McGuire, but help me help you….I’ll be more productive if I know what we’re meeting about and can prep.



Mentees, mentors, yentas: Do unto your network as you would have your network do unto you. Go forth and caffeinate!

Five leadership lessons from a horse

leader of the pack

What makes this stiletto-wearing city girl strap on boots and drive out to a barn in the burbs every week? Well, love. I married a man with a daughter who has a horse. I love my husband, I love my stepdaughter, and now I love this horse too.  He’s affectionate, wicked smart, and 1000 pounds (talking about the horse, here) so I thought I’d best start taking notes.  Here are some tips, from Caesar to me to you.

1) Be the kind of leader people want to follow

lovell profile pic

Heels are involved in this uniform

It turns out horses have an amazing BS detector, so my first lesson was be authentic. I wasted a lot of time in my early 20s (and beyond) trying to emulate others’ management styles that just didn’t fit with my own. As a young manager, I dabbled in micromanagement, and tried acting as buttoned-up as the suit-wearers in the surrounding cubicles, hiding my own humanity in the name of professionalism, attempting to seem “managerial.” These were passion-killing epic fails, for me and everyone around me. Thankfully since then I’ve rediscovered my own authentic style, and that compassion, confidence, and clarity go a long way (with horses, and people).

2) Don’t confuse dominance with leadership

Horses get this. Every herd has a dominant horse—generally kind of a jackass and a nuisance who bullies those around him into occasional submission. However, this horse isn’t the leader, as he doesn’t actually make the key decisions (like, where’s the best grass for lunch today). Deriving influence from referent authority (“do it now, because I’m the boss”) might seem to work once or twice, but that’s not the stuff of leadership, and your exhausted and annoyed team will head for the hills.  If you inspire others to follow (see #1), you’re a leader.

3) If they don’t get it, it’s probably your fault

As you can imagine, Caesar is a master of nonverbal communication, and when my elbow says canter before my words say trot, my boy’s gonna canter. I didn’t get the desired result, but that wasn’t his fault, it was mine. I communicated poorly.  If I had a dollar for all the CEOs who insisted that investors/customers/employees were stupid because they just didn’t understand their business/value proposition/directives, I’d have a pile of cash. And if I were a betting woman, I’d say that 9 times out of 10 it was because they didn’t clearly communicate their ideas.

4) Bravery isn’t being fearless, it’s having the courage to face your fears

Caesar is a ridiculously majestic and powerful animal. And he has some very palpable fears, including gusts of wind, tractors, and hospitals (mine include large dogs, clowns, and hospitals). So he was duly terrified when he had to go to the hospital last week for surgery, but didn’t flinch when the doctors and technicians poked and prodded him.  Just stood there like 1000 pounds of courage, facing his fears. I worry about leaders who describe themselves as fearless; fear is good, healthy, and must be embraced on the duly terrifying startup journey.  Similarly, vulnerability isn’t weakness.  It takes strength to be vulnerable in this crazy entrepreneurial life, and just life in general.  My favorite leaders show their humanity, vulnerability, and courage (shouts out to Rand Fishkin, Kate Matsudaira, Marc Barros and many many more).

caesar n me

Suzanne DeLyle, owner of Topline Stables, Caesar, and yours truly

5) Wait for it… you know it’s coming… here it is… get back in the saddle  

In addition to satisfying my “get back on the horse” cliché quota, I feel compelled to say I now truly understand that expression’s origin.  I’m new to this whole horse thing, but lessons were going well and I attempted to post the trot…it might not have been overly ambitious had Caesar been saddled properly, but I got dumped like my high school prom. No concussion (thanks, helmet, and butt) but pretty banged-up body and major blow to the self-esteem.  Though I’d made a mistake and took some physical and emotional punishment, I needed to restore Caesar’s faith and trust (again, he didn’t actually do anything wrong, see #3).  Leaders will make mistakes. If you don’t fail you’re not trying hard enough. Getting back in that saddle was the most painful leadership lesson on this list.  And if I were a betting woman, I’d say I’ll have to learn that one over and over again…but that I’ll most definitely enjoy the ride.




Eating my own dog food

lucy doctor

Growing up, I was always more enamored with Snoopy than the bully Lucy Van Pelt.  Though most definitely a shiksa,  she’s the kind of girl that gives “yenta” a bad name.  Much like witches, there are good yentas and bad yentas:   A good yenta provides you knowledge and wisdom about everything and a bad yenta is just an annoyance and gossip. In an homage to  Humpty Dumpty, I’ve hereby appropriated “Startup Yenta” to mean what I want it to mean: a coach and a matchmaker, which have in fact been my favorite roles in the past decade or so in the world of entrepreneurship.

Having been an entrepreneur enthusiast for this long, I figure it’s high time I take a dose of my own medicine, eat my own dogfood, and hang out my own shingle (at least as a writer). I’ve been dabbling as a contributor around town, and if history is any indication, on this site you may just hear from me on the following topics:

  • Investing
  • Startupssnoopy
  • Teams and leadership
  • Women in technology
  • Presentations and pitch competitions
  • Networking and community-building
  • Karaoke (Why? Because I love it. And it’s got great life lessons. And startup wisdom. And I love it.)

Because entrepreneurship is all about embracing uncertainty, I can’t make any promises about exactly what the future will hold. But as a fan of William Goldman’s Princess Bride,  in this blog I hope to bring you the “good parts version.”