E46 Uncovering tax credits (aka free money) for startups with MainStreet founder and CEO Doug Ludlow

In this episode, Erasmus Elsner is talking to Kshitij Grover, co-Founder and CTO of Orb (www.withorb.com), a billing platform provider that solves usage-based billing needs. The SF based startup has to date raised a total of c. $19.1 million across its Series A ($14 million led by Menlo) and seed ($5.1 million led by Greylock).

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