Kaptivate Life

Clarity for Life, Leadership, and Business

Kaptivate Life creates space to move beyond the noise, see with greater clarity, and engage more fully—with your life, your leadership, and the choices before you.

When we notice, we begin to live the life already here.

How the Work Unfolds

A simple practice of seeing and choosing

Notice

Notice

We begin by slowing the pace enough to see what is present: the question beneath the question, the patterns at work, and what may have been obscured by noise or urgency.

Understand

Understand

As the picture becomes clearer, we explore what is shaping it—your assumptions, habits, values, relationships, and the wider context around you.

Connection

Choose

Clarity creates room to respond rather than react. We identify thoughtful next steps and practices that are realistic, intentional, and genuinely yours.

Flourish

Flourish

Growth becomes less about striving to become someone else and more about living, leading, and working with greater trust in what you can already see.

Ways to Work Together

Different needs. One place to begin.

You may arrive with a decision, a transition, a leadership challenge, a business question, or simply the sense that something deserves closer attention. The work takes different forms, but it begins in the same way: creating enough space to see clearly.

01
Individual Sessions

1. Individual

Individual Sessions

A private space to slow the pace, look closely at what is asking for attention, and recognize the patterns shaping your choices. Through conversation, reflection, mindfulness, and personal development guidance, we explore opportunities for greater self-awareness, understanding, and growth—always in service of helping you see and trust what is already yours.

For some, this exploration brings practical clarity and perspective to everyday life. For others, it may also have a spiritual dimension, shaped by their own beliefs and experiences. There is no prescribed path or outcome; the invitation is to explore, discover, and grow.

What may be included

  • One-to-one conversations, in person or by video
  • Personal development guidance and self-exploration
  • Guided reflection and mindfulness practices
  • Support through decisions, transitions, or recurring patterns
  • A cadence shaped around the nature of the work
  • Optional reflections or practices between sessions
02
Small Groups

2. Group

Small Groups

Shared attention changes the quality of a conversation. Small-group sessions create room for people to listen more closely, speak more honestly, and discover what becomes visible when no one is rushing toward an answer.

What may be included

  • Facilitation of teams, communities, or simply groups of friends
  • Guided mindfulness and reflection
  • Custom themes shaped around the group
  • Practices that deepen listening and connection
  • Single sessions, workshops, or an ongoing series
  • In-person or virtual formats
  • Outdoor gatherings and field trips
03
Small Businesses

3. Business

Small Businesses

Owner-led businesses often carry their complexity personally. I work with founders, owners, and small teams to step back from the swirl, clarify what matters, strengthen communication, and make thoughtful decisions without losing sight of the people involved.

What may be included

  • Founders and owners
  • Decision framing and priority clarity
  • Management, leadership and team communication and facilitated dialogue
  • Values, culture, and ways of working
  • Planning around change, growth, or uncertainty
  • Focused projects or an ongoing advisory relationship
  • Team retreats, staff offsites
04
Leadership Perspective

4. Leadership

Leadership Perspective

Leadership asks you to hold complexity while others look to you for direction. These confidential conversations create room to see beyond the immediate pressure, examine the patterns influencing your judgment, and lead with greater clarity, steadiness, and presence.

What may be included

  • Cohesion and creativity
  • Clarity around decisions, priorities, and competing demands
  • Presence and steadiness under pressure
  • Listening, communication, and relationship dynamics
  • Perspective through a new role or transition
  • Focused engagements or an ongoing cadence
05
Business Advisory

5. Advisory

Business Advisory

Complex business questions benefit from both experience and distance. Drawing on decades across business leadership, entrepreneurship, investing, and advisory work, I help owners and leaders examine opportunities, challenge assumptions, and move forward with thoughtful conviction.

What may be included

  • Strategic perspective and decision support
  • Mindful reduction of stress points as the second point
  • Business counsel for owners, founders, and leadership teams
  • Opportunity, risk, and assumption review
  • Preparation for consequential conversations
  • A thoughtful outside perspective without a preset agenda
  • Ongoing advisory or focused decision work

About David

Seeing differently changes what becomes possible.

I was born in the Bronx to parents from the medical world, a surgeon and a nurse. Medicine, however, was not going to be my path. I discovered this in Pre-Med 101 while attempting to hit a frog on the back of the head in a science lab. Somewhere between the frog and the smell of formaldehyde came a moment of remarkable clarity: this was not for me.

So yes, I'm a New Yorker in the truest sense. I still live in New York City and feel deeply connected to it, from the NBA Champion Knicks to the other soon-to-be-champion New York teams. I love sports, competition, and everything that comes with being a fan: anticipation, disappointment, irrational hope, extraordinary highs, and the inevitable return for more. In some ways, it's not a bad metaphor for life.

But my perspective has been shaped far beyond New York. I lived in London, spent part of my life in Japan, and have traveled extensively. Different cultures, people, businesses, successes, failures, and experiences have all changed the way I see the world. I value honesty and humanity. I listen. I observe. I ask questions. And I try, wherever I am, to notice what is actually happening rather than what I expected to see.

I've been described as an optimist, an epicurean, and a long list of other things, some considerably less flattering. For a long time, I was chasing success. When I was younger, I'm not sure I could have told you exactly what success meant. I knew I wanted it. Money was certainly part of it. So were status, achievement, influence, and the satisfaction of winning. I wanted to build something, accomplish something, and have something to show for it. Some might call that ambition. Some might call it greed. Both probably contain a little truth. What I sensed even then, though, was that there had to be something more.

Over 22 years at Goldman Sachs, I experienced success in global financial markets and learned about risk, judgment, leadership, pressure, money, people, and myself. I had the privilege of working alongside extraordinarily intelligent and dynamic individuals from vastly different backgrounds and cultures. Then came a year at a hedge fund that I describe quite simply as failure. After that came more than a decade co-founding and reinventing a music technology start-up, a roller coaster of ideas, pivots, breakthroughs, "almosts," and "maybes" that ultimately ended in what we called a soft landing. In the start-up world, they generally call that failure too. And somewhere within all of this came marriage, philanthropy, entrepreneurship, and more than a decade of parenting, quite successfully thus far, although, as the British would say, you'll have to "ask the missus" about the husband part.

Somewhere along the way, my definition of success changed. Perhaps that is the most important part of the story. I no longer see life simply through the binary lens of success and failure. Both have taught me too much for either label to be particularly useful.

These days, I'm interested in something else. I teach. I sit. I notice. I live. And I help other people do more of the same. Not by abandoning ambition, achievement, leadership, or financial success. I understand those worlds too well to pretend they don't matter. But I've also learned that ambition and achievement can have a momentum of their own. You reach one goal and, almost without noticing, you're already focused on the next. There's nothing wrong with wanting more — I still do. I've simply become more interested in understanding what drives that wanting, and in being present enough to appreciate where I am before racing toward where I think I need to be.

That shift in perspective is a large part of what brought me to the work I do today. I believe there is another way to move through all of it. That is where my work begins.

I work with individuals, leaders, teams, and businesses. Sometimes I teach. Sometimes I advise. Sometimes my most useful contribution is asking the question no one else in the room is asking. And sometimes it is simply listening. I don't arrive believing I have all of your answers. I believe many of them are already there.

What I can bring is perspective, shaped by decades in global finance, entrepreneurship, leadership, mindfulness, parenting, travel, success, failure, and the experience of watching people navigate extraordinary pressure and change. My work is about creating enough space to see what is actually in front of us. To recognize the patterns we repeat. To question the stories we tell ourselves. To understand what is driving us. To become more comfortable with uncertainty. And ultimately, to make choices with greater awareness and intention.

Because mindfulness, to me, isn't about escaping the complexity of modern life. It's about learning how to be fully present within it.

So, who am I today? I have educational degrees, certifications in mindfulness and leadership, 22 years at Goldman Sachs, entrepreneurial and philanthropic experience, and decades of watching, listening, learning, succeeding, failing, traveling, parenting, questioning, and changing. All of that matters, but none of it, on its own, is the point. The point is what I've learned from it, and how I can use that experience to help you see something in yourself, your leadership, your business, or your life that perhaps you haven't been able to see before.

I'm here for that. Let's go.

Qualifications

  • MMTCP 2025 Mindfulness Certification
  • MMT 2025 Certification
  • Power of Awareness
  • Leadership Circle 360 Certification
Mindfulness Meditation Teacher Certification Program MMT 2025 Certification Greater Good Science Center
MMTCP alumnus Sounds True Leadership Circle Profile
David Kaplan

In Their Words

What clients notice

Begin with a conversation.

Schedule a time that works for you.

A first conversation is simply a chance to notice what is bringing you here, ask questions, and see whether working together feels useful. No pitch. No obligation. Just a thoughtful beginning.

Book a conversation

Opens the Calendly booking page in a new tab. Calendly's own privacy notice applies there.

Frequently Asked Questions

Have questions?

Frequently Asked Questions

What happens in a first conversation?

We'll talk about what is bringing you here, what you hope may become clearer, and whether my way of working feels useful. It is a conversation, not a sales presentation, and there is no obligation to continue.

Does Kaptivate Life offer personal development or spiritual guidance?

Kaptivate Life offers both mindfulness education and personal development guidance, supporting individuals in exploring self-awareness, personal growth and self-understanding.

While the work is grounded in mindfulness and contemplative practices, it is not affiliated with any particular religion or belief system.

Some individuals may experience aspects of this exploration as spiritual, while others approach it from a secular or practical perspective. Both are equally welcome.

Kaptivate Life does not prescribe spiritual beliefs or claim spiritual authority. Each person’s journey is their own.

Who do you work with?

I work with individuals, leaders, small groups, business owners, and small organizations. Some arrive with a specific decision or transition; others are looking for greater clarity, steadiness, or a more intentional way of engaging with life and work.

Do I need experience with mindfulness or meditation?

No. We may draw on mindfulness, reflection, or guided practice when it serves the work, but no prior experience is expected.

Are conversations in person or by video?

Both may be available. Please get in touch to confirm current in-person and virtual availability.

How long do people work with you?

There is no single required path. Some conversations are focused around a particular question; others develop into a regular rhythm over time. We will choose a structure that fits the work rather than forcing the work into a package.

Is this therapy?

No. This work is reflective, educational, and advisory. It is not psychotherapy, medical care, or a substitute for support from a licensed mental health professional.

Do you work with teams or small businesses?

Yes. Engagements can include leadership conversations, facilitated team dialogue, decision support, communication, culture, and strategic perspective, shaped around the needs of the organization.

How do I begin?

Schedule a conversation or send an inquiry. We can begin with the question that is most present for you.

How much does this cost?

There is flexibility based on time and the category of your needs. Dana is a mutual part of our work.

Get in Touch

Send a message.

If you have a question or would like to reach out directly, fill in the form below.

Please do not include medical, mental-health, financial, or other sensitive personal information in this form. If needed, we can determine an appropriate way to communicate after we respond.

Stay Connected

Follow along and join the conversation.

Proud Alumnus Mindfulness Meditation Teacher Certification Program alumnus