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Coughdrop Capital

coughdropcapital.com

“Back B2B software founders solving real problems in sales, go-to-market, product, growth, and fundraising. We bring operational expertise from both founder and investor perspectives.”

$40K – $100K
Check Size
Leads
Lead Tendency
~1 Week
Timeline
01Investment Thesis

Back B2B software founders solving real problems in sales, go-to-market, product, growth, and fundraising. We bring operational expertise from both founder and investor perspectives.

Exclusion Criteria

No consumer apps, hardware, hardware-heavy businesses, or non-software ventures

02Investment Team
SS
Stu Smith
03F4 Research Brief

Coughdrop Capital Research

Investment Thesis

Coughdrop Capital is an early-stage venture capital firm founded by brothers Austin Petersmith and Stu Smith. The fund focuses on B2B software startups at the pre-seed and seed stages. The firm's thesis centers on backing founders building software that solves real problems in sales, go-to-market, product development, and growth. The partners bring deep operational experience from both sides of the table - as founders and as investors - and provide hands-on support in these critical areas.

Sector Focus

Coughdrop invests exclusively in B2B software with a broad focus across multiple verticals:

  • Enterprise Software: HR platforms, CRM, workflow automation, compliance tools
  • Developer Tools & Infrastructure: AI/ML infrastructure, data platforms, observability tools
  • Finance & Operations: Payroll APIs, bookkeeping, fintech integrations
  • Sales & Go-to-Market: Revenue operations, deal management, sales automation
  • Healthcare Tech: Patient engagement, online therapy, healthcare services
  • Specialized B2B: Education technology, agricultural tech, supply chain tools

The fund explicitly focuses on B2B software solutions and avoids consumer apps, hardware, and hardware-heavy businesses.

Stage Focus

Coughdrop is definitively an early-stage investor with stated focus on pre-seed and seed investments. The fund emphasizes getting in at the concept stage and backing founders early with capital and operational support. The portfolio shows consistent pre-seed and seed investments with occasional Series A follow-ons for portfolio winners.

Check Size

Coughdrop writes initial checks of $40K-$100K based on stage:

  • Pre-seed: $40K-$75K
  • Seed: $75K-$100K
  • Follow-on reserves maintained for portfolio companies

This positions them as accessible to early-stage founders while maintaining check size discipline.

Lead Tendency

Coughdrop positions itself as a "first-check investor" that leads or co-leads early-stage rounds. The website explicitly states "We invest early. Here are some firms that have followed us into companies:" followed by a list of prominent VCs (Khosla Ventures, Founders Fund, Andreessen Horowitz, Y Combinator, etc.). This demonstrates strong lead positioning and the ability to attract follow-on capital from tier-1 investors.

Recent Activity

Recent portfolio investments demonstrate active deployment from 2024-2025:

  • January 2025: Pre-seed investment in AI researcher platform
  • January 2025: Pre-seed investment in data layer for financial AI
  • January 2025: Pre-seed investment in complete POS system for liquor stores
  • January 2025: Pre-seed investment in systems engineering tools
  • December 2024: Pre-seed investment in AI-powered websites for service businesses
  • December 2024: Pre-seed investment in HR-focused AI copilot
  • December 2024: Seed investment in loan origination and underwriting platform
  • November 2024: Pre-seed investment in AI character development and animation

The fund appears to be actively deploying with consistent monthly investments, primarily in AI-related B2B software.

Portfolio Highlights

Notable Exits:

  • Superhuman (acquired by Grammarly, 2017)
  • Mercury (raised to Series A, 2019)
  • Varda Space Industries (IPO, April 2024)
  • Nira (acquired by Dropbox, 2020)
  • Span (raised to Series A, 2024)
  • Serve Robotics (IPO, April 2024)
  • Symbl.ai (acquired by Invoca, 2020)

Active Portfolio (Sample):

  • Humata: ChatGPT for all your files (2024 Seed)
  • Primer: Code-first product prototyping (2024 Pre-seed)
  • Practice: Modern software for lesson-based businesses (2025 Pre-seed)
  • Hello Patient: AI-powered patient engagement (2024 Pre-seed)
  • Hamming: AI copilot for engineering delivery (2023 Pre-seed)
  • Helicone: AI observability and analytics (2023 Pre-seed)

Portfolio companies include 150+ investments with a strong track record of follow-on funding from tier-1 investors.

Team

Core Partners:

  • Austin Petersmith (Stu Smith's brother) - Co-founder and General Partner
  • Stu Smith (Austin Petersmith's brother) - Co-founder and General Partner

Both partners have deep operational experience from both founder and investor perspectives, with expertise in sales, go-to-market, product development, and fundraising. The firm emphasizes hands-on operational support for early-stage teams.

Geographic Focus

Coughdrop shows a US-centric focus with primary geographic concentration in Silicon Valley and NYC based on portfolio company locations. The fund invests primarily in US-based B2B software startups.

Founder Preferences

Coughdrop explicitly seeks:

  • Founders solving real problems in sales, go-to-market, product, growth, and fundraising
  • Both technical and non-technical founders with deep domain expertise
  • Founders with demonstrated ability to execute and scale
  • Teams with complementary skills and experience from both startup and enterprise environments

Decision Process

Coughdrop operates as a partnership with the two founding brothers as decision-makers. The fund emphasizes speed and responsiveness in decision-making, positioning itself as accessible and founder-friendly. Investment decisions appear to be made quickly to support early-stage deployment.

04Selected Portfolio
Biotech & Life Sciences
Varda·Generalproximity·Sante·Future Fields
Consumer Apps & Social
Ryze
Developer Tools & Infrastructure
String·Helicone·Coblocks
E-commerce & Marketplaces
Benable·Noto·Short Story·Project Admission
EdTech
Primer
Enterprise Software
Dalus·Ardent·Superhuman·Span·Stable·Hamming·Brev·Practice·Sacra·Magic Patterns·Humata·DealOps·Breezy·FleetWorks AI·Caledon·Milk Video·Rebolt·Rubie·Felafax·Warecorp·LDGR·Synth·Kobalt Labs·Alvva·BrandGuard·Wayfinder·Revcast·Falconer AI·Hostie·Ergo
Fintech & Payments
Primer·Mercury·Atomic·Kick·Kaaj AI
Food & Beverage
Buffalo Market
Healthcare & Digital Health
Hello Patient·Vitable Health·Benchify
HR Tech & Future of Work
Lattice·Winslow
Manufacturing & Industrial
Echo Exploration Company
Media & Entertainment
Animation·Uncovered·VStream
Real Estate & PropTech
Housable
Robotics & Automation
Serve Robotics
Security & Cybersecurity
Nira·Cloudflare·Persona
Other
Kaaj·Sotira
Open the full portfolio→
05Recent Updates

Fresh signals from public announcements, essays, and portfolio activity.

See full activity (10) →
Sacra published a dual interview with Stu and Austin Smith, brothers and founders of Coughdrop Capital, covering their origin story, angel investing approach, and views on the creator economy.
PRESS·sacra.com
AUG 7, 2026
Coughdrop Capital (via Stu Smith) invested in Hostie's $12M Series A round in July 2026, co-investing with Obvious Ventures, Gradient Ventures, Canvas Ventures, and others.
INVESTMENT·signal.nfx.com
JUL 2026
Coughdrop Capital participated in Ergo's $2.8M seed round led by FCVC, alongside Y Combinator and others. Ergo builds revenue infrastructure for AI-native GTM teams.
INVESTMENT·lhc.sbr.mybluehost.me
JUN 16, 2026
Stu Smith joined Scribble Ventures as an investor. Austin Petersmith will lead new investing at Coughdrop Capital moving forward. Stu continues supporting Coughdrop-backed founders.
TEAM CHANGE·linkedin.com
FEB 2026
Participated in Kaaj AI's $3.8M seed round for agentic AI credit intelligence platform.
INVESTMENT·linkedin.com
NOV 2025
06Frequent co-investors
SC
Shrug Capital
Both backed 4 of the same companies
Superhuman, Primer, Varda, Primer
BC
Burst Capital
Both backed 3 of the same companies
Lattice, Stable, Hostie
SV
Spacecadet Ventures
Both backed 3 of the same companies
Dalus, Primer, Practice
AG
Anthemis Group
Both backed 2 of the same companies
Atomic, Ergo
BT
Better Tomorrow Ventures
Both backed 2 of the same companies
Lattice, Mercury
Find the investors for your round→
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MV
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Quick Reference
Check Size
$40K – $100K
Stages
Pre-Seed · Seed
Decision
Partnership · ~1 Week
Warm Intro
Not Required
Involvement
Board Seat
Sector Focus
Fintech & PaymentsEnterprise SoftwareDeveloper Tools & InfrastructureHealthcare & Digital Health
Models
B2B SaaSDeveloper ToolsEnterprise SoftwareB2B
Technology
AI/MLInfrastructure
See all Fintech & Payments investors →See all Enterprise Software investors →See all Developer Tools & Infrastructure investors →
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Focus Areas
Fintech & PaymentsEnterprise SoftwareDeveloper Tools & InfrastructureHealthcare & Digital Health

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F4 Intelligence Report · Last Researched August 27, 2026F4 Research Engine