Vol. XX · No. 04July 2026 · Mill Valley, CA

Cover Story

From Kansas City to the deal seat,
told in six chapters.

Wesley Kennedy — banker, equity research analyst, fractional CFO, founder, and teacher. Two decades helping companies model, raise, and tell the story that gets them there.

Feature

A career, in six movements.

Kansas City to Santa Clara math, SVB to Wall Street research, fractional CFO to founder and teacher — and now back to the deal seat.

01

Chapter 01 · Kansas City → California

Origins

A Jesuit education and a bet on optionality

I grew up in Kansas City and was educated by the Jesuits — a place that taught me discipline, but also that the world was bigger than what I could see out the window. College was the vehicle to get out. I chose mathematics at Santa Clara because, even at eighteen, I understood real option value before I had the vocabulary for it: pick the discipline that opens the most doors, and walk through the one with the most upside. That door led to San Francisco, and to finance. My first seat was at Silicon Valley Bank, tailoring working capital for early-stage tech and life science companies — and stewarding a $25M loan portfolio through the dotcom bust with a loss ratio better than 2× the department average.

I chose math because I understood real option value before I had the vocabulary for it.
  1. Silicon Valley Bank

    2000 — 2002

    Analyst, Structured Finance

    Tailored working capital solutions for early-stage tech and life science companies; managed a $25M loan portfolio through the dotcom bust with a loan-loss ratio under 2% — 2.2× better than the department average.

02

Chapter 02 · 2002 — 2005

The Craft

Real estate as training ground, then back to tech

To go deeper on finance, I chased the fundamentals. Real estate was the best place I could find to learn modeling and valuation at a serious level — first at Ziegler Capital Markets, the #1 underwriter of continuing-care retirement communities (CCRCs), then at Green Street Advisors, the #1 shop covering REITs at the time. It was rigorous, quantitative, and unforgiving. But the excitement was elsewhere. I followed it back to technology at Thomas Weisel Partners, where I sat in a dual seat: originating convertible securities as an investment banking associate, and working alongside the prop desk pricing option-adjusted spreads for a convertible-bond arbitrage strategy.

  1. Ziegler Capital Markets

    2002 — 2003

    Investment Banking Analyst, Senior Living

    Modeled, structured, and priced $200M+ of tax-advantaged revenue bonds at the #1-ranked CCRC underwriter — including the largest issuance in the industry's history at the time. Handled Associate-level responsibilities as an Analyst.

  2. Green Street Advisors

    2003 — 2004

    Equity Research Associate, Hotels & REITs

    Supported the #1-ranked REIT research team; rebuilt the hotel group's models, cutting research publishing turnaround by 50%+.

  3. Thomas Weisel Partners

    2004 — 2005

    IB Associate, Convertible Securities

    Dual seat: originated $2B+ of convertible bond offerings on the banking side and priced option-adjusted spreads for the prop desk's convertible arbitrage strategy. Executed $500M+ of debt-for-equity swaps and refinancings.

03

Chapter 03 · 2006 — 2013

Deals & the Three Cs

M&A, SaaS research, and the language of narrative

M&A at Ridgecrest sharpened the deal instinct — acquirer landscapes, merger models, business-development pitches. Leading SaaS equity research at Tier1 Research (later acquired by the 451 Group, then S&P) taught me how public markets listen to a software story. I launched coverage on Concur, NetSuite, and Salesforce, and authored some of the first deep dives on SaaS unit economics. Then I hung my own shingle. Over the next several years, I served as fractional FP&A leader to more than twenty companies — most of them on-premise businesses transitioning to on-demand SaaS — and, more importantly, helping them tell that story to boards, investors, and acquirers. The pattern I kept seeing: the winning narratives are always three things — clear, compelling, and credible.

The winning narratives are always three things: clear, compelling, and credible.
  1. Ridgecrest Capital Partners

    2006 — 2007

    M&A Associate

    Built acquirer landscapes and merger models with full accretion-dilution analysis; led business development pitches to mid-market tech and consumer clients.

  2. Tier1 Research (→ 451 Group → S&P)

    2007 — 2009

    Lead Equity Research Analyst, SaaS

    Launched coverage on Concur, NetSuite, and Salesforce.com. Authored some of the industry's first deep dives on SaaS efficiency metrics (CAC ratio, burn multiple). A contrarian read on SaaS delivered 59% annualized returns on long/short recommendations.

  3. Independent Consulting

    2009 — 2013

    Fractional FP&A / Finance Partner

    Fractional finance partner to 20+ SaaS and high-growth companies — building the plans, systems, and investor narratives that carried them through fundraises, transitions, and exits. It's where the Three Cs became a working philosophy.

04

Chapter 04 · 2014 — Present

Founder

The operating seat, from zero to scale

In 2014, I put the analytical toolkit to work as a founder. My wife recognized an unmet need for specialized training for prenatal and postpartum women, and we co-founded The Lotus Method. She built the practice; I brought the operating discipline, the financial model, and the investor story. We raised over $5M — half of it non-dilutive — and scaled to seven brick-and-mortar locations at peak. The company is now positioned for sale. I know what the founder's chair feels like: the 3 a.m. model stress, the board pitch, the recap, the exit. That empathy is hard to teach — and it is exactly what makes me credible across the table.

I know what the founder's chair feels like. That empathy is hard to teach.
  • The Lotus Method — Capital

    2014 — 2019

    Co-founded with my wife; raised $5M+, half of it non-dilutive, on a category-defining thesis for prenatal and postpartum training.

  • The Lotus Method — Scale

    2019 — 2024

    Scaled to seven brick-and-mortar locations at peak, launched the company's first digital offering, and drove a $4M net increase in annual revenue post-recap — returning the business to profitability and positioning it for sale.

05

Chapter 05 · Ongoing

Teacher

If you can explain it, you understand it

Teaching has been the throughline. At the Investment Banking Institute I launched the San Francisco location and taught finance and investment banking to analysts and associates; at iXperience I taught U.S. students in Cape Town, South Africa, and online. Every class forced me to take a complicated idea — a DCF, a convertible, a SaaS unit-economics story — and make it digestible. That skill is not a side note; it is the same skill required to build a board deck, a sell-side memo, or a management presentation.

The ability to make a complicated idea feel simple is not a side note; it is the craft.
  • Investment Banking Institute

    Ongoing

    Launched the San Francisco location; taught finance and investment banking to analysts and associates.

  • iXperience

    Ongoing

    Taught U.S. students in Cape Town, South Africa, and online — translating Wall Street concepts into actionable, real-world frameworks.

06

Chapter 06 · Woodside Capital Partners

The Right Fit

Two lanes, one throughline: Main Street meets software

This is why the next chapter is M&A advisory at Woodside Capital Partners — and I know exactly where I'd hunt. My first lane is digital health, wellness, and femtech. I'm not covering it from the outside: I co-founded a women's health company, raised over $5M — half of it non-dilutive — scaled it to seven locations, and I am running its sale process right now. I know the buyers, the multiples, and the diligence questions because I'm living all three. My second lane is the software making Main Street more efficient — vertical SaaS, payments, and embedded fintech for SMBs. Here I bring something rare in a banker: I was the customer. Across seven locations, I ran the business on the booking, POS, payments, payroll, and marketing stack this category sells — I know which products owners can't live without, and which get churned the first hard quarter. Layer on two decades of SaaS fluency — research coverage of Concur, NetSuite, and Salesforce; fractional finance inside 20+ software companies, including Metaswitch (acquired by Microsoft) and commerce-enablement names like Carthook — and the thesis is simple. An MD hire is a revenue bet, so here is mine: 25+ founder, board, and investor relationships in exactly WCP's sweet spot — founder-led companies approaching their first process, who need their story made clear, compelling, and credible.

Two lanes I've lived, not just covered: I built a Main Street business — and ran it on the software I'd now be selling.
  • Digital Health, Wellness & Femtech

    Founder-operator credibility

    Co-founded, capitalized ($5M+, half non-dilutive), scaled to seven locations, and currently positioning for sale. Direct overlap with WCP's digital health, behavioral health, and wellness coverage — in an underbanked niche a boutique can own.

  • Main Street Tech

    Evaluated from the buyer's side of the invoice

    The software, payments, and embedded fintech running local businesses — evaluated from the buyer's side of the invoice. Seven locations operated on the full SMB stack, plus commerce enablement work at Carthook.

Dispatches

The craft, distilled.

Two decades across banking, research, and operating seats — the disciplines I bring to every engagement.

  • 01M&A Advisory & Sell-Side Process
  • 02Financial Modeling & Valuation
  • 03Capital Raising & Deal Structuring
  • 04Investor & Board Narratives
  • 05Financial Planning & Analysis
  • 06SaaS & Subscription Economics
  • 07Strategic Planning
  • 08Teaching & Mentoring

Credentials

Education.

  • Golden Gate University

    2001

    M.S., Economics

  • Santa Clara University

    1999

    B.S., Mathematics

Correspondence

The next chapter starts with a conversation.

Location
Mill Valley, CA