#185: Survived COVID and a PE Exit —A Travel Tech Founder's Journey - Steve Reynolds

Summary of #185: Survived COVID and a PE Exit —A Travel Tech Founder's Journey - Steve Reynolds

by Greg Head

1h 0m•February 27, 2026
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Overview of #185: Survived COVID and a PE Exit — A Travel Tech Founder's Journey — Steve Reynolds

This episode of the Practical Founders Podcast (host Greg Head) features Steve Reynolds, founder and former CEO of TripBam, a travel‑tech company that automated hotel (and later air) reshopping and contract auditing for corporate travel buyers. Steve walks through founding TripBam, pivoting from B2C to B2B, surviving COVID, running a profitable, capital‑efficient company, and the eventual sale to Emburse (backed by K1). He shares practical lessons about product-market fit, pricing, dealing with legacy travel systems, and the tradeoffs of raising external capital.

Key facts & metrics

  • Company: TripBam (founded ~2013 as B2C; pivoted to B2B early)
  • Sold: 2023 to Emburse (private equity–backed by K1)
  • Revenue at exit: roughly $8–10M ARR
  • Customers: ~2,000 corporate customers sending bookings; ~250 large corporate direct clients
  • Employees at peak: ~50 (US + Europe)
  • Largest customer: Amazon (hotel spend ~ $600–700M)
  • Pricing models: subscription, transaction fee (~$1/booking), or gain‑share (TripBam kept ~25% of savings)
  • Target ROI for customers: ~8x (800%)
  • VC raised: ~$1.5M seed (Thayer Ventures) — later pivoted to cash‑flow growth rather than heavy fundraising
  • M&A advisor: GLC (Denver) — Adam Haynes
  • Post‑acquisition: Steve moved into a chief strategy role, rolled over some equity, sold some rollover shares but retained some equity in Emburse

What TripBam did (product & value)

  • Core offering: automated reshopping of hotel (and later air) bookings to capture lower rates after initial booking, plus contract auditing to ensure negotiated discounts were applied.
  • Data sources: tapped multiple hotel distribution channels (GDS, channel partners) rather than just crawling hotel websites.
  • Automation: rebooked reservations automatically (when possible) or notified travelers/travel managers about better rates.
  • Value:
    • If staying in same property: 5–10% hotel spend savings.
    • If open to alternate hotels: 25–30% savings.
    • Auditing hotel contracts often produced more long‑term value (identifying contract misapplication).
  • UX: Minimal traveler disruption — automated or near‑automated changes and an email notification to travelers.

Go‑to‑market & sales motions

  • Early demand drivers: trade shows, buyer luncheons hosted by large customers (IBM, others) and peer referrals.
  • Sales focus: sold mainly to travel managers initially, then CFO sign‑off for large contracts.
  • Sales tactics: free pilots importing customers’ future bookings to demonstrate real, provable ROI.
  • Pricing playbook: designed in reverse from ROI — price to deliver ~8x return so CFOs would approve quickly.

Founder's background & career arc

  • Steve’s background: computer science + MBA; long career in travel tech (systems consulting at Ernst & Young, founding CTI which sold to Amex, Travel Technologies Group).
  • Team: co‑founders included experienced technical partner(s) (e.g., Caleb Blanton) and prior working relationships that accelerated execution.
  • Approach: pragmatic, cash‑flow focused founder who preferred bootstrapping/earned growth over large rounds of dilution.

Surviving COVID & operational resilience

  • COVID impact: transactions fell to near zero quickly; subscription revenue and conservative cash management helped TripBam survive; PPP assistance and early right‑sizing aided survival.
  • Business resilience: company retained most customers through COVID; demonstrated stickiness and ability to withstand shock — a credibility point in the later sale process.
  • Philosophy: planning for worst‑case events (9/11, pandemic) influenced conservative pricing and revenue mix to ensure durability.

The exit & post‑acquisition experience

  • Process: sale process started pre‑COVID, paused, resumed later; process took ~9 months total (longer than anticipated).
  • Buyer: Emburse (PE‑backed by K1); deal included rollover equity for founders.
  • Integration: Emburse’s early post‑acquisition management shakeup (K1 replaced management) changed strategic direction — Emburse opted to integrate travel assets closely with expense product rather than keep travel standalone.
  • Founder role: Steve became chief strategy officer with limited operational role, eventually left Emburse (fully out by July following acquisition timeline).
  • Outcome: sale price aligned with expectations; some rollover proceeds sold, some retained pending future Emburse exit.

Travel industry context & technical constraints

  • Legacy plumbing: airlines, GDS (Sabre), and hotel property management systems are decades‑old and complex, creating integration friction and slow modernization.
  • TMCs (Travel Management Companies) like Amex GBT, BCD create distribution/relationship dynamics that can resist change or slow third‑party integrations.
  • Competitive moat: signing many of the largest corporate accounts (250 big logos) created a defensible position because TMCs and hotels can’t easily neutralize service without industry‑wide coordination.

Views on fundraising & founder tradeoffs

  • Steve’s stance: prefer following cash flow, avoid over‑raising and dilution. Being majority owner of a smaller yet profitable exit can be more meaningful than a tiny stake in a “hockey stick” funded venture.
  • Tradeoffs: outside capital shortens investor horizons and can shift strategy to short‑term growth targets; bootstrapped/cash‑flow models preserve strategic control and upside.

On AI and the future of travel tech

  • Current AI impact: mostly voice‑to‑text, chatbots, basic text interfaces — limited transformational impact yet.
  • Largest near‑term AI opportunity: customer support (handling disruptions without long hold times), not necessarily core booking plumbing because of legacy backend systems.
  • Long horizon: AI will become more pervasive, but integration with legacy systems will remain a gating factor.

Practical advice Steve gives founders

  • Consider alternatives to raising capital — money often finds you if the solution is real and visible.
  • Use pilots with real customer data to prove ROI (a tangible pilot beats promises).
  • Price to deliver clear ROI (e.g., aim for 8x) to speed buy‑in from procurement/CFOs.
  • Keep optionality — when pivoting, retain a fallback/escape hatch if the new path doesn’t work.
  • Expect M&A to take longer and be more work than hoped; prepare for integration risk and cultural change post‑acquisition.
  • Build businesses that can survive shocks (recessions, regulatory or global events) through conservative cash management and sticky contracts.

Notable quotes

  • “I tend to follow the cash flow.”
  • “Once you start taking outside money, you get someone else starting to make those decisions for you, whether you like them or not.”
  • “If you can survive COVID, you can survive anything that’s going to come your way.”

Actionable takeaways (for practical founders)

  • If selling to enterprises: run a real pilot using customers’ live data to prove ROI before asking for a contract.
  • Price to demonstrate an obvious payoff to the CFO (high ROI makes procurement approvals fast).
  • Preserve equity where possible — small profitable exits can be personally meaningful.
  • Build for durability: subscription or mixed revenue that cushions transaction volatility helps survive black‑swan events.
  • Anticipate integration risk in M&A: find out how the acquirer plans to treat your product and team before closing.

This episode is particularly useful for founders building enterprise SaaS in legacy industries: clear examples of product‑led value, go‑to‑market tactics for large buyers, conservative capital strategy, and realistic expectations about M&A and post‑acquisition integration.