

Startup Project: Build the future
Nataraj
Conversations with founders, operators and investors who are building the future. Listen to find the stories, ideas, tactics & investments behind the products that will define the future of technology.
https://startupproject.substack.com/
https://startupproject.substack.com/
Episodes
Mentioned books

Aug 27, 2023 • 50min
#62 Ashmeet Sidana - Founder of Engineering Capital on Investing in Technical Insights
In this episode of the podcast, we feature Ashmeet Sidana, the founder and Chief Engineer of Engineering Capital. Ashmeet has an extensive background in engineering and venture capital, with experience as the Director of Product Management at VMWare and as a venture capitalist.
During the conversation, Ashmeet discusses various topics, including his experience developing the ESx Server at VMWare and leading seed rounds of companies like Azure Power and Tubi. He also shares insights into why venture capitalists prefer startups to stay private and the importance of investing in technical insights.
Ashmeet also talks about his approach to getting in front of future founders and explains why he chooses not to invest in blockchain. He discusses the significance of large funding rounds in the AI seed stage and the value of investing in open-source companies.
To learn more about Ashmeet Sidana and his perspectives on investing in startups with technical risks, you can listen to the full episode on platforms like YouTube, Spotify & Apple.
Full conversation includes:
- Being Director of PM at VMware & Venture Capitalist
- Developing ESx Server at VMWare
- Leading seed rounds of azure power (public & valued at $2B)
- Leading seed investment at Tubi
- Starting Engineering capital
- Why vcs want startups to stay private
- What it means to invest in technical insights
- Getting infront of future founders
- Not investing in blockchain?
- Large funding rounds in AI seed stage
- Investing in opensource companies

Aug 6, 2023 • 54min
#61 Joe Heitzeberg - From Tech Whiz to Sustainable Meat Entrepreneur
To stay up to date checkout thestartupproject.io & follow Nataraj on twitter: @natarajsindam and on LinkedIn at https://www.linkedin.com/in/natarajsindam
Join us in this captivating episode as we sit down with Joe Heitzeberg, a multifaceted entrepreneur who has navigated the world of technology and business with remarkable success. From his early days in the tech industry to founding his acclaimed venture Crowd Cow, Joe shares his incredible journey and valuable insights on various topics.
1. Joe's Entry to Technology
2. Working for Paul Allen
3. Import Furniture Business
4. Opportunity Cost of MBA
5. Building Viral VoIP App for MySpace
6. Selling Media Piston to Upwork
7. Starting Crowd Cow
8. Problems with Chicken in the U.S
9. Fundamental Shifts from AI
10. AI Tinkerers
Follow Joe on LinkedIn at https://www.linkedin.com/in/joeheitzeberg
To stay up to date checkout thestartupproject.io & follow Nataraj on twitter @natarajsindam and on LinkedIn at https://www.linkedin.com/in/natarajsindam

Jul 2, 2023 • 1h 4min
#60 Tim Chen - From Open Source Contributor to Investor in Infrastructure Startups
Tim Chen is the Managing Partner at Essence VC, an early-stage fund focused on data infrastructure and developer tool companies. He has over a decade of experience leading engineering in enterprise infrastructure and open source communities and companies. Prior to Essence, Tim was the SVP of Engineering at Cosmos, a popular open source blockchain SDK. Prior to Cosmos, Tim co-founded Hyperpilot with Stanford Professor Christos Kozyrakis, leveraging decades of research to disrupt the enterprise infrastructure space, which later exited to Cloudera. Prior to Hyperpilot, Tim was an early employee at Mesosphere and CloudFoundry. He is also active in the open source space as an Apache Software Foundation core member, maintainer of Apache Drill and Apache Mesos, and CNCF TOC contributor.

Jun 3, 2023 • 31min
#59 - Aseem Datar - Partner at Madrona Ventures - From Intern to General Manager at Azure
Aseem joined Madrona in 2021 after spending almost twenty years as an operating executive. He works alongside founders building the future of next-generation infrastructure (core, security, DevOps), intelligent applications, robotics, and automation.
Full conversation includes:
From Intern at Windows to GM at Microsoft Azure
GM at Azure to Investing at Madrona
Investing at Madrona
Startups vs Big Tech in AI
Commoditization of LLMs
Difference between LLMs & Human Brains
Follow Aseem on LinkedIn at https://www.linkedin.com/in/aseemdatar/
To stay up to date checkout thestartupproject.io & follow Nataraj on twitter: @natarajsindam

May 21, 2023 • 50min
#58 - TA McCann - Professional Sailor, Serial Entrepreneur (5x Founder with 3 Exits), Managing Director at Pioneer Square Labs
To stay up to date checkout thestartupproject.io & follow Nataraj on twitter: @natarajsindam
T.A. McCann is a serial entrepreneur with an impressive track record. He has founded and served as CEO of several successful companies. Some notable ventures include Senosis (acquired by Google), Gist (acquired by Blackberry), and Rival IQ, a leading company in marketing analytics.
McCann's expertise extends beyond founding companies. He has also held senior roles at Microsoft, where he led divisions such as Exchange and the Mobile Services divisions. Additionally, he has worked as an EIR (Entrepreneur in Residence) at Polaris Venture Partners and Vulcan Capital.
Full conversation includes:
Becoming a professional sailor
Working at microsoft exchange
Starting 5+ companies (3 exits)
Working for Paul Allen & building Startup Studio Vulcan Labs
Selling Gist to Blackberry
Rival IQ
Synosis (acq by Google)
Pioneer Square Labs
Systematic customer discovery & customer development process
Advice to entrepreneurs raising capital
Is AI a step change?
Who will capture value in AI? Big tech or startups?
Follow TA on LinkedIn at https://www.linkedin.com/in/tamccann/

May 14, 2023 • 6min
#57: How to Run Innovation Sessions with Bill Gates to Solve World Problems?
To stay up to date checkout thestartupproject.io & follow Nataraj on twitter: @natarajsindam
In this episode Nataraj spoke to Taylor Black who co-founded Fizzy Inc. Post Fizzy Taylor worked at Innovation Science Fund & currently works as a Principal Product Manager at the Office of the CTO Incubator at Microsoft.
Transcript:
[00:00:00] Nataraj: I looked at the portfolio there then
it's completely deep tech, uh, and sort of like invention based, uh, ideas.
[00:00:08] Nataraj: Uh, so what was the process of like
capturing and invention and taking and productizing it and, you know, making a
return out of it? Like what was the thinking process there?
[00:00:20] Taylor: So the, uh, and you can read Malcolm
Gladwell's take on this in a, in an article where he described our invention
sessions. Um, a and the invention sessions are a bit of a riff on like an
innovation session or an envisioning session or things along those lines where
you, you come up with wild ideas within a particular problem space, um, in a
very unfettered sort of, Um, and the whole goal of this session is to generate
as many ideas as possible.
[00:00:52] Taylor: That's the sole ROI you're looking for
in those sessions. Um, but there's certain conditions you set for success in
those [00:01:00] sessions. And so the way that
we ran those sessions, and I, and I, I ran, uh, a number of them, um, is that
we would prepare for months ahead of time in gathering all of the materials
that related to the problem.
[00:01:14] Taylor: and by materials I mean the scientific
research in a particular problem space, the, uh, market, uh, and startup landscapes
of that particular problem space. Um, uh, things that people had written about
it. Books, articles, um, you know, YouTube videos, everything, uh, along those
lines. And the goal was to, um, inform.
[00:01:43] Taylor: Kind of the fermentation moment of
when you're thinking about a problem, all of these things w wouldn't
themselves, um, not be a solution necessarily, but there are all the things
that someone who wanted to be completely informed or as, as, as informed and
possible as possible about a set of [00:02:00]
problems. Um, Had all of the raw material there.
[00:02:03] Taylor: We'd also do customer discovery, we'd
do customer interviews to understand those pain points. We'd bring people in,
um, uh, and run sessions with them where they would, you know, get deep into
their own, um, the problems they were encountering so that everybody who is,
and everybody who's part of the sessions had to.
[00:02:22] Taylor: Understand those materials, uh,
deeply. We'd even quiz them on occasion. Um, it also helped that, uh, bill
Gates, um, uh, whenever he came to those sessions, he would have all of those
materials like completely groced. And so you, you know, you needed to have them
groced too so that you didn't, you know, uh, lose face in front of Bill.
[00:02:44] Taylor: But, um, Uh, but the key, so we'd,
we'd get everybody, all of those materials and have them go through them, uh, a
good month or so before the actual sessions happened. Um, that gave everybody
an, an even playing [00:03:00] field in terms
of, you know, I may be a physicist, I may be a biz dev person, I may be, um, an
attorney.
[00:03:06] Taylor: I may be, uh, you know, a program
manager, but I have all of the same raw material. Uh, and my own perspective on
it that I can bring to these sessions. The sessions themselves, them, um, were
set around particular problem spaces and we'd start, we'd start each, um,
session and then there's a variety of different kinds of sessions that we ram.
[00:03:28] Taylor: Um, Uh, with a lot of provocations, a
lot of conversation, a lot of like wild thinking and post-it notes and
whiteboards of just dumping ideas out, uh, that had occurred to people or
occurred in conversation or happened in the, in the hallway outside. Um, and we
get all those ideas down, documenting everything.

May 7, 2023 • 3min
#56: Why Wordpress dominates internet?
#56: Why Wordpress dominates internet?

Apr 30, 2023 • 3min
#55: What is the insurance against Innovation Dilemma?
To stay up to date checkout thestartupproject.io & follow Nataraj on twitter: @natarajsindam
In this episode Nataraj spoke to Taylor Black who co-founded Fizzy Inc. Post Fizzy Taylor worked at Innovation Science Fund & currently works as a Principal Product Manager at the Office of the CTO Incubator at Microsoft.
Transcript:
[00:00:00] Nataraj: To me it always made sense for large
companies to have some kind of incubator or accelerator model because one of
the reasons I think we are seeing in this bear cycle, sort of like when the
wave sort of, you know, falls down, you see who's naked scenario.
[00:00:17] Nataraj: Um, I think any company which
survives multi decades has to have multiple large businesses. Mm-hmm. . I think
in a lot of ways, I mean, looking back, a lot of companies didn't, uh, look for
long-term opportunities as much as they should. Like we can talk about like,
uh, Amazon, you know, putting billion dollars into their phone, but I would
argue the potential on the upside of suckers was so high they should have put
in, you know, one more billion and tried the next version.
[00:00:50] Nataraj: Mm-hmm. . Mm-hmm. , uh, and I. , like
argue the same with Facebook in a sense. Like now they're doing this metaverse
thing. [00:01:00] Um, and sort of again
retreating that back now. But I feel like even Facebook with all its cash flow,
uh, didn't really think, um, because they always self constrained themselves to
be a social company.
[00:01:14] Nataraj: Um, like I think that's sort of like
a self-imposed mental model on themselves. Mm-hmm. , like, uh, I would not
impose themselves like a social company. Yeah. You work good at Facebook and
WhatsApp, but I mean, look at how many great technologies that came out from
Facebook, open source community and like putting that social as a blanket on
your company.
[00:01:34] Nataraj: I think. Set a backstage for all
these technologies, which could be, you know, productionized and, you know,
capitalized. Mm-hmm. . Right. Uh, that's, I feel like a lot of companies,
especially the large companies, are with very good cash flow sort of mixed out
on business opportunities because of that reason.
[00:01:50] Nataraj: That's my personal view on like, , a
lot of companies could have it if it is well run. Mm-hmm. . Um, and should have
it because of this reason. Right? Mm-hmm. , it's sort of [00:02:00] like you are the innovation dilemma that
you'll encounter at some point as a large company, and you have to have a sort
of a backup backstopping mechanism to that innovation dilemma, which every
company will eventually face.
[00:02:12] Nataraj: Mm-hmm. , um, So I feel like the
innovation, uh, accelerator or the incubator would sort of act as that, uh, you
know, that part of small investment, it's sort of like an insurance to the, uh,
to innovation dyna that you would eventually encounter anyways, uh,
[00:02:28] Taylor: , I think you're right.
[00:02:28] Taylor: There's a, there's an inherent problem
there too, though, is that, um, uh, innovation is inherently a yo low yield. .
Um, and so within, and it's my kind of rule of thumb, that within two or three
years of any program like ours existence, um, finance is gonna come and say,
where's the revenue? Where's the roi? And if you don't have a data driven way
of showing your, your anticipated revenue, your anticipated ROI on the basis of
your activities, then uh, [00:03:00] it's entirely
legitimate that you get.
[00:03:02] Taylor: There's a, there's a, there's data
driven ways of showing that the whole venture ecosystem depends on the fact
that you're able to show future revenue on the basis of what you're doing now.
Uh, that's how you raise funds, right? Um, and so every, uh, innovation program
inside an enterprise has to have that same data-driven hygiene.
For full conversation check out Episode 53.

Apr 23, 2023 • 4min
#54: How Techstars Seattle Works & How Should Founders Think About It?
To stay up to date checkout thestartupproject.io & follow Nataraj on twitter: @natarajsindam
In this episode Nataraj spoke to Marius Ciocirlan who co-founded ShareGrid, a marketplace for filmmakers and photographers to rent and sell their equipment. It was acquired by Backstage and is now Managing Director of Techstars Seattle. Techstars expanded to Seattle in 2010, and since then more than 130 companies have gone through the program & collectively gone on to raise more than $2.5 billion in capital.
Full Transcript:
[00:00:00] Nataraj: So Techstars is an, you know,
traditionally what we call as an accelerator, right? Yeah. Uh, so what are the
founders really getting outta, um, joining tech?
[00:00:09] Marius: Yeah, for sure. So, um, the Tech
Techstars program essentially, uh, falls into almost three phases. So it's a 13
week program and it's kind of, uh, set up in three phases. The first phase is
customer discovery, so we worked with you to ensure that like, , you truly
understand who your customer is and what are they buying from you.
[00:00:31] Marius: Like, you know, you, you would be
surprised how many people have an idea of who their customer is, but it's not
clearly defined. They don't really understand why that customer is interested
in their product. So even companies that are farther along, we find. , it's
always good to like really reflect on who your customer is.
[00:00:50] Marius: So the first phase is customer
discovery. Second phase is go to market and execution, which is more important
nowadays, especially given the market [00:01:00]
situation. More important than ever to actually gain real traction in your
business and prove out that your business has some product market fit. And
product market fit can mean different things at different stages.
[00:01:12] Marius: But at least in your initial M V P,
there needs to be some product market fit. And then the third phase is we're
preparing you to go out in front of investors. So we're working on your pitch
deck, we're working on your delivery, we're working on all of your documents,
uh, getting you ready to ensure that you're ready for, uh, investors and
putting you in front of investors.
Full version at thestartupproject.io

Apr 16, 2023 • 56min
#53 Taylor Black - Innovation Science Fund & Microsoft Incubator
To stay up to date checkout thestartupproject.io & follow Nataraj on twitter: @natarajsindam
In this episode Nataraj spoke to Taylor Black who co-founded Fizzy Inc. Post Fizzy Taylor worked at Innovation Science Fund & currently works as a Principal Product Manager at the Office of the CTO Incubator at Microsoft.
Full Conversation includes:
Starting a company during law school
Running a WordPress server farm
Why WordPress still dominates internet?
Working at Innovation Science Fund
Running innovation sessions attended by Entrepreneurs, Nobel laureates, Scientists & Bill Gates
Fundamental technology breakthrough in Metamaterials
Funding Starlink competitor
Incubator inside Microsoft for the Office of the CTO
Measuring Innovation inside large organizations
You can connect with Taylor here on LinkedIn.


