Jumpmaster Profile

Laurel Touby

Laurel Touby is the founding partner at Flatiron Investors. Flatiron Investors is a group of 20-odd Founders and high net worth individuals. They are sophisticated investors who meet monthly to work on deals together. Laurel and her team source deals, do the diligence and run the operations. Their concentration is: BtoB, SaaS, and FinTech.

Prior to Flatiron Investors, Laurel founded mediabistro.com, a BtoB that revolutionized the way people in the media industry do business, connect and communicate. During her time as CEO, she pulled the company through two recessions, pivoted, managed growth with minimal resources and developed audience via guerrilla and social marketing (before that term existed). Following the sale of the company for $23 mm to Jupitermedia, Laurel remained with the company through June, 2011.

HAVE YOU IN THE PAST HAD OR DO YOU CURRENTLY HAVE A PROCESS TO THAT HELPS GUIDE YOUR DECISION MAKING? SPECIFICALLY, DO YOU OR HAVE YOU USED A PROCESS TO DEFINE CLEAR, REALISTIC AND ACTIONABLE GOALS AND TRACK YOUR ABILITY TO ACHIEVE THEM? YES/NO IF YES, PLEASE EXPLAIN:

No. I wish I could say that I did. I think I succeeded based on sheer ambition and perseverance. I took a short seminar on Getting Hired in college and put all that wisdom to work for myself. It got me my first few jobs, but when it came time to run a business, those lessons did not apply. I had a lot to learn about management styles, leadership, etc. and I learned the hard way (employees threatened mutiny at one point.)

CAN YOU IDENTIFY WHEN YOU FIRST HAD CAREER GOALS THAT WERE CLEAR AND ACTIONABLE AND WITH REALISTIC OBJECTIVES?

21-25 years old

COMPLETE THIS SENTENCE: I’ve used process / practices to get from zero to $10 mm in sales at my company (mediabistro.com)

WHICH 3 PERSONAL VALUES/ QUALITIES HAVE YOU RELIED ON MOST MAKE YOUR FIRST BIG CAREER JUMP?

  1. CLARITY
  2. FOCUS
  3. DISCIPLINE, PLANNING
  4. VISION
  5. PURPOSE
  6. GRIT / RESILIENCE / TENACITY

Discipline and Planning, Vision, and GRIT/RESILIENCE/TENACITY!!

BRIEFLY EXPLAIN:

Even if I didn’t end up where I thought I was going, I was clear, determined and focused on a goal. I envisioned the goal and every activity I embarked upon was in service to that goal. I spent most of my waking life working. I took very little time off and I was working night and day to move forward in my career.

CAN YOU DEFINE A TIME/ POINT WHEN SENSE OF PURPOSE BECAME A PART OF YOUR GOALS AND PLAN?

I always had this going for me, from a very young age. Escaping from Florida and going to a fantastic college in the Northeast was the start. After that, working in media and rising in that career and finally starting a tech company in the mid-90s and successfully growing it. Now, I am entering the Venture community, facing new challenges and using the same level of determination and doggedness to get where I need to go. I always had to work twice as hard because I had no natural allies in any of the fields I entered.

WHICH OF THE FOLLOWING BEST DESCRIBES YOUR APPROACH TO HELPING OTHERS COACH AND SUPPORT THE GOALS AND OBJECTIVES OF THEIR PEERS?

  1. I HAVE A DISCIPLINED AND THOROUGH APPROACH TO ENSURING PEER COACHING BY LEADERS
  2. NATURAL LEADERS WILL RISE- IDENTIFYING AND RETAINING THEM IS ESSENTIAL
  3. I FOCUS ON HIGH LEVEL MESSAGING TO PROVIDE BETTER ENGAGEMENT AND MOTIVATION

C – I try to motivate people via messaging and one-on-one conversations. I am not currently running a company, so I am not helping others coach and support their peers. Leading by example is the best way to impart your values to others.

WHICH OF THE FOLLOWING METHODS DO YOU USE MOST OFTEN TO BROADEN YOUR OWN INSIGHTS AND CHALLENGE YOUR MENTAL MODELS?

  1. ASKING QUESTIONS OF OTHERS AND RECEIVING CANDID FEEDBACK
  2. READING LEADERSHIP BOOKS AND ARTICLES
  3. ENGAGING IN FORUM STYLE DISCUSSION WITH MY PEERS
  4. NONE OF THE ABOVE / DESCRIBE

A and B.

I read broadly, mostly newspapers and Twitter. I am trying to expand my reading into uncharted areas so as to hear what is going on in the other (red) part of the country, too. I ask tough questions of others and listen to their feedback and try to do this calmly and without prejudice. Then, I try to put their suggestions into practice in my daily life.

WHICH OF THE FOLLOWING BEST DESCRIBE YOUR APPROACH TO SHARING STORIES OF YOUR FAILURES:

  1. I OPENLY DISCUSS MY FAILURES WITH MY TEAM
  2. I FOCUS ON DISCUSSION ON SUCCESS AND CITE THE FAILURES WHEN IT SUITS MY NEEDS
  3. I RARELY DISCUSS MY FAILURE

I am probably too open about discussing my failures.

DO YOU CITE FAILURES OR SETBACKS AS A PART OF YOUR LEADERSHIP COMMUNICATION WITH YOUR TEAMS? YES / NO

YES

WHICH OF THE BELOW BEST DESCRIBES WHY YOU THINK YOU FAILED OR HAVE SETBACKS:

  1. LACK OF CLARITY SELF-AWARENESS
  2. LACK OF FOCUS
  3. LACK OF DISCIPLINE / PLAN
  4. LACK OF VISION OR SKILLS
  5. LACK OF PURPOSE

I think success takes time. Sometimes you are not on the same time trajectory as your success and you give up too soon. When I have failed, it was probably because I gave up before I could succeed.

WHICH OF THE FOLLOWING BEST DESCRIBES HOW YOUR THOUGHT PROCESS REGARDING BUSINESS AND LEADERSHIP HAS CHANGED IN THE PAST 10 YEARS:

  1. NOT AT ALL
  2. VERY LITTLE
  3. A SUBSTANTIAL AMOUNT

C – I don’t know that this exact question applies, since I am now in a completely different business than I was before (I used to be in media and after that I led a startup).

I used to manage completely differently. It wasadifferent time then and millennials had not yet entered the workforce. Now, I am far more sophisticated and patient about leading a team, about growing a company, so many things.

DO YOU HAVE A METHOD OR PROCESS TO CHALLENGE YOUR OWN ASSUMPTIONS AND DETERMINE YOUR FLAWS AND NEEDS? I DON’T / I DO

I do.

IF YES – DOES IT REGULARLY HELP GUIDE YOUR LEARNING?

  1. SOMEWHAT TRUE
  2. VERY TRUE
  3. NOT TRUE
  4. VERY TRUE

B – Very True

DO YOU HAVE OR HAVE YOU EVER HAD A SAFE/PRIVATE ENVIRONMENT (FORUM OR COACH) WHERE YOU CAN EXPRESS YOUR EMOTIONAL WEAKNESSES AND GET SUPPORT TO BETTER ASSESS AND IMPROVE THEM? YES / NO

No

WHEN YOU CONSIDER THE BIG DECISIONS THAT LED TO YOUR HABITUAL SUCCESSES, YOU ARE YOU ABLE TO IDENTIFY, EXPLAIN OR DESCRIBE A THOUGHT PROCESS THAT YOU USE TO ASSESS, INFLUENCE AND EXPEDITE YOUR DECISION MAKING?

The best way to make a big decision is with thoughtful consideration and input from others. I don’t have a specific way to assess, influence or expedite decision-making. I am a Creative. I do a lot from my gut and not as much via a conscious process.

Track Your Jumps

Because leaders with focus and discipline jump farther and faster.