Clara Ma started out in recruiting, spent almost three years as the generalist at a four-person Bollywood dance fitness company, then ran operations at AngelList before becoming chief of staff at Hugging Face when it was ten people. She stayed through the Series B and the run to forty five. After two years building On Deck's Chief of Staff Fellowship, she gave herself a three-month sabbatical, kept circling back to the same subject, and started Ask A Chief of Staff from the road in October 2022. She had made three placements by December. This is a conversation about when a founder actually needs a chief of staff, how that role differs from an operations hire, and the habit of asking people about their plans long before you need anything from them.

In this episode, we cover:

→ The signal that it is time to hire a chief of staff, and when the answer is a functional hire instead
→ How a chief of staff differs from a general operations role: the mandate is the principal
→ Engineered serendipity, and why she kept finding openings before they were ever posted
→ Done is better than perfect, and getting a rough first draft in front of people for buy-in
→ What community members say they want versus what they actually stay for
→ Why consistency on LinkedIn pays off even when nobody likes or comments

Chapters:
00:00 - Meet Clara Ma, founder of Ask A Chief of Staff
02:32 - Political science, media studies, and the law school that never happened
05:14 - First job in recruiting, and learning to spot potential
09:07 - Three years as the generalist at a four-person company
14:11 - Hitting the ceiling, and landing at AngelList
18:50 - Discovering the chief of staff role
21:01 - Chief of staff at Hugging Face, from ten people to forty five
27:55 - Done is better than perfect
30:20 - Running the On Deck Chief of Staff Fellowship
32:40 - Engineered serendipity, and asking who is leaving
39:01 - Burnout, a sabbatical, and accidental entrepreneurship
44:40 - Why the community had to come after the placements
51:27 - When a founder should actually hire a chief of staff
53:35 - Chief of staff versus a general operations hire
57:33 - Growing on LinkedIn when nobody is engaging

Host: Dar Patel, Founder of Little Pursuits
Connect: https://www.linkedin.com/in/darpatel/
Join Founder Circle, our small-group coaching for seed-stage founders: https://littlepursuits.life/apply/
Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/

Guest: Clara Ma, Founder of Ask A Chief of Staff

Nomiki Petrolla got a D minus in economics, restarted college from scratch, and went on to lead product at an AI company while running a consulting practice on the side for ten years. Theanna, her community-plus-software platform for women founders, is her fifth business: two dropshipping companies died in three months each, and a one-on-one coaching practice became the blueprint for something bigger. This is a conversation about why the product is only 10% of the business, building your own distribution through founder-led content, and growing a company without burning out.

In this episode, we cover:

→ The illusion that building a product is building a business, and why the product is 10% of the job
→ How AI made building easier and everything else ten times harder, starting with distribution
→ She used to glorify founders who raised millions: what changed her mind
→ Testing the idea with a WhatsApp group of ten people before building the app
→ Founder-led content as the distribution channel no tool can replace, and why you have to suck at it first
→ Hustle without burnout, plus hiring a contractor before a full-time role

Chapters:
00:00 - Meet Nomiki Petrolla, founder of Theanna
06:15 - The D minus that made her restart college
17:45 - Glorifying founders who raise millions, then changing her mind
22:47 - Four businesses before Theanna: consulting, dropshipping, coaching
27:56 - Test the idea with a WhatsApp group of ten
32:15 - The product is 10% of the business
34:01 - Founder-led content is your distribution channel
38:27 - Hustle without burnout
44:53 - Getting your first customers is the hardest part
49:23 - Community plus software, the hill she will die on

Watch the full conversation: https://youtu.be/BNSmaY2tkOQ

Host: Dar Patel, Founder of Little Pursuits
Connect: https://www.linkedin.com/in/darpatel/
Join Founder Circle, our small-group coaching for seed-stage founders: https://littlepursuits.life/apply/
Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/

Guest: Nomiki Petrolla, Founder of Theanna
Connect: https://www.linkedin.com/in/nomikipetrolla/

Zach Forester tested badly all through school, walked away from the mortgage company he co-owned when it started costing him his health, and cold-called his way into Uber when it had about 50 drivers. His black-car fleet became Uber's driver-training partner, over 150,000 drivers and a 16-year partnership later, and today he builds Optium, automating and offshoring back offices for other companies. This is a conversation about hiring for the trait and teaching the skill, finding the next business inside the one that is collapsing, and the inner work that kept him going through thousands of failures.

In this episode, we cover:

→ The hiring rule behind his fleet and 150,000 trained Uber drivers: hire the trait, teach the skill
→ Cold-calling Uber at about 50 drivers, and why he credits luck and curiosity over strategy
→ Delegation in hyper growth: even if you want to own it, you have to give it up
→ When Lyft erased his moat, the next business was already inside the old one
→ Don't believe the AI hype, from a founder who sells automation
→ A decade of Jungian analysis, a yoga practice he refused to skip, and ideas that arrive away from screens

Chapters:
00:00 - Meet Zach Forester, founder of Optium
01:48 - Testing badly in school, and German as the way in
17:58 - Business owner at 29, in a market in freefall
21:43 - Walking away from the mortgage industry for his health
24:55 - First client Goldman Sachs, then a cold call to Uber
29:07 - The secret sauce: hire the trait, teach the skill
33:58 - Lyft erases the moat, and the pivot hiding inside the business
38:07 - A garage sale leads to an autonomous vehicle company
44:14 - Don't believe the AI hype, from an automation founder
46:06 - I've failed thousands of times

Watch the full conversation: https://youtu.be/3ttQQ1VB8HM

Host: Dar Patel, Founder of Little Pursuits
Connect: https://www.linkedin.com/in/darpatel/
Join Founder Circle, our small-group coaching for seed-stage founders: https://littlepursuits.life/apply/
Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/

Guest: Zach Forester, Founder of Optium
Connect: https://www.linkedin.com/in/zach-forester/

Stephanie Simpson left full-time teaching in 2021 to build a portfolio coaching business, bringing a background in dance and psychology to how she helps leaders and founders work with stress instead of against it. This is a conversation about reinvention, the difference between a mentor and a sponsor, and why the people who last fall in love with the problem, not their solution.

In this episode, we cover:

→ Why most businesses fail: the founder falls in love with the solution and stops listening to the market
→ The difference between a mentor and a sponsor, and why a sponsor says your name in the rooms you are not in
→ Why a bad relationship with stress can actually kill you, and what a healthy one looks like
→ What coaching actually is: why a good coach talks only 20 percent of the time
→ The dance lesson that reframes every setback
→ Why every founder needs a coach, not just a mentor

Host: Dar Patel, Founder of Little Pursuits
Connect: https://www.linkedin.com/in/darpatel/

Join Founder Circle, our small-group coaching for seed-stage founders: https://littlepursuits.life/apply/

Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/

Taya Kudashkina grew up in Siberia with an engineering degree and a dream of Silicon Valley, built startups across the United States and Russia, then left everything behind after the invasion of Ukraine and rebuilt her career from zero in a new country as an angel investor. This is a conversation about reinvention, starting over with no network, and what investors really look for in early-stage founders.Hit subscribe to join our community of builders!In this episode, we cover:→ The values exercise she used to reinvent herself: list every path, then try each one on by talking to people already living it→ Why Silicon Valley treats failure as normal, and how different that felt from the shame she grew up with→ Why a six-month financial cushion is the real key to reinventing your career, especially for women→ What angel investing actually is, and how to start small through syndicates for as little as two thousand dollars→ The real question every early-stage investor is asking: can this founder deliver→ Why so few women are in the room, and the risk-aversion she wants to change for her daughterChapters:00:00 - Meet Taya Kudashkina, angel investor02:16 - Chasing Silicon Valley from Siberia12:55 - Silicon Valley's failure mindset vs the shame she grew up with17:07 - A $2M raise, a failed startup, and the darkest time of her life19:46 - Resilience: letting the hard moment pass27:47 - Leaving Russia and starting from zero in Luxembourg30:37 - The values exercise: trying on careers to find the next step43:03 - What angel investing is, and how to start small51:22 - What she looks for in a founder56:24 - Why so few women are in the roomSubscribe to Little Pursuits for raw stories from founders, leaders, and experts: https://www.youtube.com/@littlepursuits?sub_confirmation=1Watch Next: https://youtu.be/v8LrIQaRhyIHost: Dar Patel, Founder of Little PursuitsConnect: https://www.linkedin.com/in/darpatel/Join Founder Circle, our small-group coaching for seed-stage founders: https://littlepursuits.life/apply/Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/Guest: Taya Kudashkina, Angel InvestorConnect: https://www.linkedin.com/in/taisiyakudashkina/#Startups #Founders #Entrepreneurship #Leadership #Business #podcast

Dave Zager built his first skills fixing computers his dad broke on purpose, then talked his way into one of the only consulting jobs offered out of a few hundred campus candidates during the 2003 downturn. Twenty-two years later he is a partner at Deloitte, and the mindset that got him there has not changed: ask the honest worst case, then decide. This is a conversation about staying calm under pressure, letting go as you rise into leadership, and shifting your own luck.Hit subscribe to join our community of builders!In this episode, we cover:→ Growing up building and breaking things: how his dad's rule, "if you can fix it, it's yours," shaped a career in tech→ Landing a consulting job out of a few hundred candidates during a brutal 2003 market, and why he believes you can shift your own luck→ The worst-case question he asks his team before every hard decision, and the anchor that makes it work→ What separates the leader you trust from the leader you don't, learned in the early days of COVID→ Letting go as you rise: the hardest transition from doing the work yourself to trusting a team to do itChapters:00:00 - Meet Dave Zager, partner at Deloitte02:41 - Garbage trucks, street hockey, and "if you can fix it, it's yours"11:17 - Prodigy, AOL, and downloading his first MP3 over a semester20:54 - Landing one job out of a few hundred candidates, and shifting your own luck37:29 - Why you become untouchable once you've survived hard things42:48 - The worst-case question he asks his team before a hard decision44:46 - His anchor: waking up alive, and why nobody remembers the decision in a week48:42 - The leader he trusts versus the leader he doesn't55:11 - Career stages: analyst to manager to partner, and learning to let go1:15:40 - Everyone's problems on a clothesline: the comparison trapSubscribe to Little Pursuits for raw stories from founders, leaders, and experts: https://www.youtube.com/@littlepursuits?sub_confirmation=1Watch Next: https://www.youtube.com/watch?v=De9rU87jwyEHost: Dar Patel, Founder of Little PursuitsConnect: https://www.linkedin.com/in/darpatel/Join Founder Circle, our small-group coaching for seed-stage founders: https://littlepursuits.life/apply/Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/Guest: Dave Zager, Partner at DeloitteConnect: https://www.linkedin.com/in/davezager/#Startups #Founders #Entrepreneurship #Leadership #Business #podcast

Emily Kyle spent her career in marketing, including at GitLab, after a winding path through art history and law school. When her father died suddenly and she hit the isolating, archaic paperwork of settling his estate, she quit with no plan and went all in on Good Grief Co, a company built to guide people through the administration of loss. This is a conversation about grief and reinvention, building a company from your own hardest experience, talking to users before you build, and what fundraising feels like as a woman.Hit subscribe to join our community of builders!In this episode, we cover:→ Why not making a choice is still making one, and how her father's death forced hers→ Turning the isolating paperwork of loss into a company, Good Grief Co→ Falling in love with the problem instead of your solution, after interviewing over a hundred people→ Why post-death administration, and the fact that 75 percent of people die without a will→ Building an MVP that was too robust, and designing for a grieving brain→ What asking for money feels like as a woman, and finding a circle of female foundersChapters:00:00 - Meet Emily Kyle and Good Grief Co04:01 - From art history and law school to marketing26:01 - Her father's last day: a home run and a heart attack27:32 - The wake-up, and quitting with no plan36:16 - Why is every loss so paperwork-driven?38:35 - Going all in on Good Grief Co40:21 - Falling in love with the problem, not the solution49:09 - A human problem, and finding a co-founder1:00:27 - One year in: the product is live1:05:17 - Why the fundraising ask feels different for womenSubscribe to Little Pursuits for raw stories from founders, leaders, and experts: https://www.youtube.com/@littlepursuits?sub_confirmation=1Watch Next: https://youtu.be/w782j02rMbAHost: Dar Patel, Founder of Little PursuitsConnect: https://www.linkedin.com/in/darpatel/Join Founder Circle, our small-group coaching for seed-stage founders: https://littlepursuits.life/apply/Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/Guest: Emily Kyle, Founder & CEO of Good Grief CoConnect: https://www.linkedin.com/in/emilylucie/Good Grief Co: https://www.linkedin.com/company/good-grief-co/#Startups #Founders #Entrepreneurship #Leadership #Business #podcast

Sukhpal grew up between India and Canada, taught himself to code as a teenager, and spent two years at IBM before a string of layoffs pushed him to bet on himself. He saved $250,000 in a year, built 38 products, sold one company in 30 days, and now runs Carousel Studio, the number one app on the Canva marketplace, used by a quarter of a million people. This is a conversation about building in public, the real math of starting a company, and refusing to stay a nobody.

Hit subscribe to join our community of builders!

In this episode, we cover:

→ The note he found in his Evernote: "I don't want to be a nobody," written twice, six months apart

→ How he saved $250,000 in a year by stacking three or four dev contracts at once

→ The ladders of wealth: moving from trading time for money to owning a product

→ Why he built 38 products and writes a postmortem for every one that failed

→ Selling a company in 30 days on Acquire.com, and the simple SaaS valuation math

→ Building Carousel Studio into the number one Canva app, and the pivot that unlocked it

Chapters:

00:00 - Meet Sukhpal and his journey

00:31 - Growing up between India and Canada

02:27 - Teaching himself to code

05:37 - Android apps and the one that went viral

08:01 - IBM and the developer advocate role

11:18 - Learning sales: the math class and the mall job

14:40 - Improv and comedy podcasts

18:02 - Engineering vs science, then getting laid off

20:29 - The 4% raise problem

21:26 - "I don't want to be a nobody"

23:07 - Saving $250K to quit

28:54 - Why everyone should be a builder now

33:58 - The ladders of wealth and stacking contracts

36:04 - OnDeck and the pricing breakthrough

38:29 - 12 startups in 12 months

41:34 - B2B vs B2C and the math

49:46 - Building in public and the surface area of luck

56:04 - Reframing failure: start 100 things

1:05:21 - Selling a company in 30 days

1:10:15 - Carousel Studio, the number one Canva app

1:15:24 - Resources he recommends

1:17:00 - Buying 12 coaching sessions upfront

Subscribe to Little Pursuits for raw stories from founders, leaders, and experts: https://www.youtube.com/@littlepursuits?sub_confirmation=1

Watch Next: [related episode URL]

Host: Dar Patel, Founder of Little Pursuits

Connect: https://www.linkedin.com/in/darpatel/

Join Founder Circle, our small-group coaching for seed-stage founders: https://luma.com/littlepursuits

Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/

Guest: Sukhpal, Founder of Carousel Studio

Connect: [guest LinkedIn URL]

#BuildInPublic #Startups #FounderMindset #SaaS #Bootstrapping #podcast

Ruben Austin moved from Germany to the US to play college football, then started his first company out of visa necessity and never looked back. He has founded and sold an early influencer marketplace, invested in startups, advised governments, and now builds in the experience economy with All in All, a referral-only leadership network, and Origin, an immersive yoga brand. This is a conversation about failing forward, why most founders should never raise, and building real relationships in business.Hit subscribe to join our community of builders!In this episode, we cover:→ Coming to the US for college football, then starting a company out of visa necessity→ His first exit: building an early influencer marketplace and the lessons that outlasted it→ Failing forward, founder syndrome, and what actually makes an investor say yes→ Bootstrap vs venture: why most founders should never raise money→ Building in the experience economy: a no-soliciting leadership network and an immersive yoga brand→ Don't guard your network: why generous introductions come back to youChapters:00:00 - Meet Ruben Austin00:30 - Growing up in Germany and the lure of American brands02:57 - How American football brought him to the US04:53 - Finding his real passion in business11:44 - Becoming a founder out of visa necessity14:06 - His first company: an early influencer marketplace17:57 - Failing forward and knowing what not to do20:10 - Surviving the early grind with coaching and criticism24:14 - Founder syndrome and why coachability matters27:39 - What investors look for in a founding team30:54 - You don't need to reinvent the wheel35:01 - Should you raise? Why most founders shouldn't38:23 - How AI lowered the barrier to building45:28 - Building All in All, a leadership network46:46 - Why business networking is broken51:11 - Curating real experiences: art, books, longevity, music53:40 - Origin: an immersive yoga brand1:08:21 - Resources: coaches, fractional leaders, and showing up1:16:14 - The one book he recommends to every founder1:21:04 - Don't guard your networkSubscribe to Little Pursuits for raw stories from founders, leaders, and experts: https://www.youtube.com/@littlepursuits?sub_confirmation=1Watch Next: https://youtu.be/TS3ww8mS-p8?si=MAV0AD7Gkd6dBrxYHost: Dar Patel, Founder of Little PursuitsConnect: https://www.linkedin.com/in/darpatel/Join Founder Circle, our small-group coaching for seed-stage founders: https://luma.com/littlepursuitsNewsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/Guest: Ruben Austin, Founder of All in All and co-founder of Origin Connect: https://www.linkedin.com/in/rubenaaustin/#Entrepreneurship #Startups #VentureCapital #Networking #Leadership #podcast

Maria Shum pivoted from fashion retail through product roles at Electronic Arts, Meta, and Adobe, then sat on a startup idea for three years before building Lila, an AI stylist for life's big events. This is a conversation about reinventing your career and building an AI product from zero to one.

Hit subscribe to join our community of builders!

In this episode, we cover:

→ Pivoting from fashion to tech: how to spot which skills transfer and close the gaps

→ Breaking into product management the old-school way, before coaching programs existed

→ Navigating interviews and internal transfers at big tech companies like Meta and Adobe

→ The origin of Lila: from a frustrating digital closet to an AI stylist

→ Building zero to one: turning an "ugly search bar" into conversational AI by reading user signals

→ Knowing when a product is real, choosing one signal, and why she is waiting on revenue

Chapters:

00:00 - Meet Maria and Lila, the AI stylist

00:40 - Growing up in her mom's retail store

02:05 - The 2008 crisis and the pivot from fashion to tech

05:25 - How to identify which skills transfer

12:58 - Breaking into product the old-school way

18:37 - Interviews and internal transfers at Meta

26:24 - The startup idea she sat on for 3 years

28:37 - The digital closet idea and why it failed

30:54 - The pivot to Lila, the AI stylist

34:09 - Why search is not enough: the pregnancy example

38:03 - Zero to one and the "disappointing" first feedback

40:23 - The prom dress moment that reshaped the product

46:30 - What users actually care about: the results

50:13 - When is a product really finished?

55:35 - Honing the signal and waiting on revenue

Subscribe to Little Pursuits for raw stories from founders, leaders, and experts: https://www.youtube.com/@littlepursuits?sub_confirmation=1

Watch Next: [related episode URL]

Host: Dar Patel, Founder of Little Pursuits

Connect: https://www.linkedin.com/in/darpatel/

Join Founder Circle, our small-group coaching for seed-stage founders: https://luma.com/littlepursuits

Newsletter: The Inner Game, on the inner game of building and leading: https://littlepursuits.substack.com/

Guest: Maria Shum, Founder of Lila (AI stylist)

Connect: https://www.linkedin.com/in/mariashum/

#AI #ProductManagement #Startups #FemaleFounders #CareerChange