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A place to talk about startups, venture capital and tech. For a full download, double-click on sandhillroad.io
58 Episodes
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In this episode, Erasmus Elsner is talking to Richard White, the serial entrepreneur behind Uservoice and Fathom.video. Richard is a design engineer and product visionary who has been in the first YC batch with Justin Khan and Emmett Shear for Kiko (YC S05) and most recently came back to the YC W21 to see how startup kids are doing the tricks today.
00:00 Intro
00:51 Who is Richard White
03:40 The power of cold emails
05:09 Kiko (YC S05)
08:53 The UserVoice journey
12:09 Traction and funding
16:09 UserVoice today
$18:16 Starting Fathom
22:28 The Fathom product
27:35 Fathom customer profile
30:27 Fathom in remote orgs
32:03 Richard's own use of Fathom
33:57 Fathom integrations
36:14 Zoom Marketplace + platform risk $
39:20 Going through YC (again)
42:57 Fathom seed round
46:11 The fun of fundraising
47:28 Vision for Fathom
In this episode, Erasmus Elsner is talking to Gen Isayama, co-founder and CEO of World Innovation Lab, a Palo Alto and Tokyo based venture firm investing in growth-stage companies and serving as a bridge between startups and Japanese corporations.
00:00 Intro
01:30 World Innovation Lab
04:10 From Japanese lawyer to Silicon Valley VC
09:10 From DCM to WIL
13:55 WIL investment thesis
19:40 Japanese entrepreneurial culture
26:57 Open innovation Models at WIL
31:57 Raising Fund I
37:00 Full spectrum of WIL Activities
42:16 Investment strategy and portfolio construction
48:06 Outlook for WIL III
51:23 Call to action
In this episode, Erasmus Elsner is talking to Dan Ahrens, founding partner at Left Lane Capital, a New York based venture capital and early growth equity firm that invests in high-growth internet and consumer technology businesses.
00:00 Intro
02:43 Consumer vs. enterprise tech
05:09 Getting into venture
07:54 Raising Left Lane I
10:35 Investing while fundraising
13:09 The Left Lane Capital playbook
17:09 Due diligence in a hot market
18:52 Scaling Left Lane Capital
21:36 Deployment pace
23:28 Focus area
26:04 Hard conversations
28:10 Arc
32:53 Exo Freight
35:28 Supply Chain Tech
37:04 Call to action
In this episode, Erasmus Elsner is talking to Divyang Arora, founder and CEO of Byte Kitchen about cooking up the future of digital food halls with Byte Kitchen founder Divyang Arora.
0:00 Intro
1:24 2 minute elevator pitch
4:27 Going all in
8:07 Business Model
14:52 The Byte Kitchen playbook
18:52 Optimal Partner Restaurant Profile
25:39 End customer benefits
27:25 Raising the Seed Round
30:14 Early traction
31:54 Byte Kitchen's Use of Tech
34:50 Call to Action
In this episode, Erasmus Elsner is talking to Michael Crandell, CEO Bitwarden about scaling open-source password manager Bitwarden.
00:00 Intro
00:50 What is Bitwarden
03:22 From side hustle to venture-backed
06:36 Joining a Bootstrapper at Series A
09:58 Open-source GTM
13:25 Open-source defensibility
15:35 Community vs. enterprise edition
17:37 Revenue traction
19:51 Competition
22:25 Fundraising journey
25:46 Use of funds
28:25 Go-to-market strategy
31:40 Building a remote-first company
35:11 Arbitrating talent
36:00 Next steps for Bitwarden
38:28 Not the first time at the rodeo
In this episode, Erasmus Elsner is talking to Kyle Harrison, general partner at Country about everything from the economics of whale hunting, the venture product offering to his recent joining of Contrary.
00:00 Intro
01:11 Way into venture
04:58 Time of reflection
07:24 The under-innovated venture model
10:46 Your fund size is your strategy
16:16 The nature of the general partnership
20:38 Rethinking the org chart
25:13 VC product vs. VC service
28:31 VC product industry practice
31:13 From monolithic brands to solo capitalist
37:18 The future of venture tribes
39:52 Joining Contrary
In this episode, Erasmus Elsner is talking to Doug Ludlow, co-founder and CEO of MainStreet, which helps startups and small businesses uncover tax credits.
00:00 Intro
01:05 Hipster
05:09 Happy Home Company
07:10 Starting MainStreet
11:22 The nature of Tax credits
16:03 The Path Act
17:52 The MainStreet Product
19:14 Customer success stories
20:41 Customer profile
22:40 Audit protection / guarantee
24:13 Moats
25:37 Whitespace vs. Switching
26:30 MainStreet traction
27:47 Fundraising
28:17 Pre-empted Series A
30:22 MainStreet layoffs
32:42 Unit economics
33:42 Unit economics
34:50 Vision for MainStreet
37:42 Fast five
39:01 Call to action
In this episode, Erasmus Elsner is talking to Kelsey Bishop founder and CEO of Candor, which is a nexgen, authentic social network.
00:00 Intro
01:02 What is Candor
03:25 Single player mode
03:56 Kelsey’s background
06:19 Employee-culture fit
08:31 Getting started
10:31 Migrating from bubble
11:38 Raising the Seed
12:42 Getting pre-empted
13:50 Raising from angels
15:23 Solo founder journey
16:58 Product + traction
21:47 Business model
23:03 Talking to users
24:51 Remote first company
26:25 Becoming a CEO
27:03 Call to action
In this episode, Erasmus Elsner is talking to Abhishek Nayak the co-founder and CEO of Appsmith, which is an open-source, low code internal tool builder. 00:00 Intro
03:15 Entrepreneur in Residence at Accel
05:52 Third time at the Rodeo
09:55 Validating a startup idea at his wedding
11:38 Built for Internal facing apps
13:48 The Appsmith Customer Persona
15:06 From Dataset to app
15:42 What Appsmith is replacing
17:07 The Appsmith killer feature
18:29 Getting to the first 100 users
21:40 Customer love + product iteration
23:07 Competition
25:24 Open source vs. closed source
27:53 Open source applications vs. infrastructure
31:07 Open core model
34:12 Traction and metrics
36:43 Metrics tracked over time
37:43 Fundraising for 3rd time
39:27 Fundraising journey
43:50 Remote company discounts
45:27 Call to action
In this episode, Erasmus Elsner is talking to Chon Tang, the founding GP of the Skydeck Fund. Chon is an experienced Silicon Valley engineer, entrepreneur and investor. He was formerly founding partner and Managing Director of Junzi Capital Engineering, a leading quantitative hedge fund investing in the commodity space. He has been actively investing in Silicon Valley startups for 12 years, and has personal investments in over 25 deals with multiple IPOs and exits.
00:00 Intro
03:40 Starting a tech company in 2000
09:27 Founder-investor transition
17:51 The art of talent arbitrage
22:09 Raising Fund II
27:00 Portfolio construction
30:40 Skydeck Fund entry point
32:50 Success stories
37:00 Skydeck Accelerator Program + Challenges
41:00 The accidental VC
45:00 Next Skydeck batch
In this episode, Erasmus Elsner is talking to Shmulik Fishman, founder and CEO of Argyle, about raising the Series A through an investment memo and the firm’s mission of making user-permissioned employment data ubiquitous and reinvent credit decisioning for lenders and consumers.
00:00 Intro
00:56 What does Argyle do?
03:17 Experiencing the pain point
06:48 Raising the Series A with an investment memo
11:41 Automated form population
14:05 Real-time income/employment verification
17:52 Status quo: credit bureaus
22:18 Technical/data moats
26:59 Standing on the shoulders of giants
28:40 API integrations
30:28 Screen scraping vs. API scanning
32:41 Traction and metrics
35:26 Pricing Strategy
38:36 Argyle Team
41:36 Remote-first valuation discount/premium
In this episode, Erasmus Elsner is talking to Seth Sternberg the co-founder and CEO of Honor, which is a managed marketplace for in-home care that has recently announced a USD 370m Series E led by Baillie Gifford.
00:00 Intro
01:19 Elevator pitch
02:19 Original inspiration
05:28 The Meebo experience
08:06 Serial founder problems
09:06 Getting the founder team together
10:52 The Honor MVP and marketplace model
14:52 Marketplace supply side
19:44 Marketplace demand side
21:57 Fundraising journey
25:07 Growth capital rounds
27:07 Expansion strategy
28:56 Homestead acquisition
31:45 Competitive landscape
31:45 Competitive landscape
34:08 GTM and growth strategies
In this episode, Erasmus Elsner is talking to Casey Fenton, founder of Couchsurfing and Upstock, about the early days for Couchsurfing when Casey was pioneering what has since become known as the “sharing economy” and how is is now bringing the sharing economy to the cap table with Upstock.
00:00 Intro
01:13 The Couchsurfing proof-of-concept
02:46 The first Couchsurfing stay
03:49 501(c)3 non-profit status
06:34 The mechanics of the benchmark Series A
06:34 The mechanics of the benchmark Series A
08:27 The Couchsurfing MVP
10:38 The donation-based model
11:58 The demand side monetization model
15:34 The chicken-and-egg question
17:11 Casey’s philosophy on ego hacking
21:11 Building for the internet without ego
23:57 Upstock
28:34 Ideal customer moment
30:20 Switching costs
31:09 Competitors and integrations
33:40 Milestone-based equity kickers
35:03 Following Casey’s work
In this episode, Erasmus Elsner is talking to Andrew Gazdecki, founder of MicroAcquire. The episode was recorded when MicroAcquire was still a fully bootstrapped one person company. A few weeks later MicroAcquire announced that it had raised a $6.3m Seed round led by Bessemer Ventures.
00:00 Intro
01:09 What is MicroAcquire?
02:55 Buying a micro-SaaS as a learning experience
05:15 Andrew’s own founder path
10:40 Key bootstrapper metrics
14:53 Solving the chicken-and-egg problem
19:17 Supply side: company profiles
20:24 Marketplace discovery vs. transaction facilitation
22:45 Microacquire marketplace monetisation
26:51 Microacquire as a curated marketplace
30:12 Dealing with inflated seller asks
33:25 Disrupting the business broker industry
35:45 Competitor marketplaces
36:50 Scaling Microacquire
38:10 Raising venture capital vs. bootstrapping
In this episode, Erasmus Elsner is talking to Queenly co-founders Trisha Bantigue and Kathy Zhou about building a consumer marketplace and tackling the formalwear industry.
00:00 Intro
00:56 The Queenly Elevator Pitch
01:52 Launching Queenly during lockdown
04:04 The pageant dress market
08:06 Formal wear resale market microstructure
10:16 The Queenly minimum viable product
12:37 Go to market strategy
14:56 Queenly marketplace metrics
16:36 The Queenly fundraising journey
20:40 Raising $6.3m From Andressen Horowitz
22:58 Solving the marketplace chicken and egg problem
24:58 Unlocking supply
27:02 Offering power seller tools to boost supply
28:15 Cracking the demand side
29:12 Facilitating Marketplace Transactions
31:36 Marketplace take rate
32:43 Competition And Playbook
35:16 Formal wear Price dynamics
38:22 The Queenly Vision
00:00 Intro
00:24 Welcome to Miami
01:08 Operators Podcast
03:21 Finding the right guests
06:54 Delian’s founder/operator
08:22 Cohort analysis with Keith at Square
10:30 Nightingale
12:24 Operating experience at Teespring
14:24 Varda Space
17:45 Splitting time between Varda and FF
19:45 Varda Space incubation
23:50 Delian as an investor at Founders Fund
27:07 Faire
30:56 Tiger Global and the rise of crossover funds
35:31 Hyperscaling
36:45 Moving to Miami
39:45 Keeping up with Delian
In this episode, Erasmus Elsner is talking to Remote.com founder Job van der Voort about building the future of remote work.
0:00 Intro
00:49 The first two years of Remote
02:19 Preparing for the perfect Storm at Gitlab
06:17 Leaving Gitlab
10:47 Business model
14:10 Legal war chest
15:20 Fintech-payment layer
16:20 SaaS layer
17:52 Pricing
19:47 Competitive landscape
24:12 Seed round
25:42 Series A
28:37 Remote best practices
31:52 Enabling random bump ins
34:07 The remote company handbook or “bible”
35:23 Remote company stack
36:20 Asynchronous vs. synchronous work
40:19 Remote for startups
In this episode, Erasmus Elsner is talking to Sheel Mohnot, co-founder of Better Tomorrow Ventures about his journey as a founder, angel investor and co-founder of Better Tomorrow Ventures.
00:00 Intro
01:11 Guest appearance on a Justin Bieber/Ariana Grande music video
03:16 The “pronoia” mindest
03:16 The “pronoia” mindest
05:04 Sheel’s background
07:56 The Pitch
12:12 Investing with founder authority
14:16 500 Startups fintech fund
18:25 Fintech thesis and sector evolution
22:09 Fintech backend
23:43 Better Tommorrow Ventures
29:24 Differentiation
32:52 Reserve capital
34:52 The good, the bad and the ugly investments
37:40 Sheel-defining investment
41:10 …the bad and the ugly
In this episode, Erasmus Elsner is talking to Reeves Wiedeman, author of "Billion Dollar Loser: the epic rise and fall of WeWork".
00:00 Adam's intro
01:11 Intro
01:38 Adam Neumann
04:11 Adam's art of persuasion
05:41 Book title
08:10 Writing process
13:01 WeWork evolution and business model
16:21 Tech vs. real estate company
19:25 WeWork community
22:01 WeWork funding journey
25:11 JPMorgan round
26:50 Masa and the Softbank round
30:39 Acquisitions and side businesses
33:16 Valuation and comps
36:59 Public persona and IPOs
38:50 WeWork today
40:07 Staying in touch with Reeves
In this episode, Erasmus Elsner is talking to Kyle Lui, Partner at DCM, about the recent IPO roll that DCM has been on. The Menlo Park-based firm has generated a 61x return on investments that have gone public in the past two years. Kuaishou is the standout, with its market cap to entry valuation at 2,000x.
00:00 Intro
00:50 Who is Kyle Lui
01:33 Intro to DCM
03:30 DCM IX and the A-Fund
05:36 Differentiation through US-Asia angle
07:45 DCM's Japan strategy
08:48 DCM's recent roll
10:00 Biggest winner Kuaishou
11:07 All three sides of the table
14:01 Choicepass
15:36 First 5 years at DCM
18:52 Docsend investment
21:47 Lime investment
23:57 Him’s and Hers investment
26:05 D2C unit economics
28:13 Keeping up with what Kyle is up to
29:33 Kyle's investment focus areas
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