---
title: "Career change and angel investing | Ali Omar | Negotiator 35"
titleOriginal: "Uran vaihto Enkelisijoitukset | Omar | #neuvottelija 35"
episodeNumber: "35"
guest: "Ali Omar"
datePublished: 2020-09-04
duration: "48:50"
youtube: "https://www.youtube.com/watch?v=7F2wctXu-ls"
captionsVtt: https://www.neuvottelija.com/podcast/episodes/ep35-uranvaihto-ja-enkelisijoittaminen-ali-omar/captions.en.vtt
captionsSrt: https://www.neuvottelija.com/podcast/episodes/ep35-uranvaihto-ja-enkelisijoittaminen-ali-omar/captions.en.srt
originalLanguage: "fi"
topics: ["investing_markets"]
subtitleMethod: "none"
provenance: "Owner page upgraded on 2026-08-30 with a MacWhisper Finnish transcription (582 cues, entity pass run from the archived raw; the previous 03-Final copy had only trailing whitespace stripped). Chapters come from the publisher's own YouTube chapter list, verified cue-by-cue against the transcript; two timecodes were out of order in the source list and were corrected against the cues. The previous chapter list was a fabricated constant 150-second grid and has been replaced. Subtitles are Finnish only; no English cue track shipped."
fiCanonical: "https://www.neuvottelija.fi/fi/episodes/41-uran-vaihto-enkelisijoitukset-omar-neuvottelija-35"
canonical: https://www.neuvottelija.com/podcast/episodes/ep35-uranvaihto-ja-enkelisijoittaminen-ali-omar/
---
# Career change and angel investing | Ali Omar | Negotiator 35

## Chapters

- [00:00](https://www.youtube.com/watch?v=7F2wctXu-ls&t=0s) Cold open: an intensive investor and B2B software
- [00:29](https://www.youtube.com/watch?v=7F2wctXu-ls&t=29s) Introducing Ali Omar
- [00:44](https://www.youtube.com/watch?v=7F2wctXu-ls&t=44s) From doctor to founder of Med Group
- [01:12](https://www.youtube.com/watch?v=7F2wctXu-ls&t=72s) Zero to a hundred million with Kustaa Piha
- [01:41](https://www.youtube.com/watch?v=7F2wctXu-ls&t=101s) A provocative LinkedIn post about changing careers
- [02:23](https://www.youtube.com/watch?v=7F2wctXu-ls&t=143s) Why career changers walk into the jaws of death
- [02:44](https://www.youtube.com/watch?v=7F2wctXu-ls&t=164s) Tacit knowledge and underrating your own competence
- [03:38](https://www.youtube.com/watch?v=7F2wctXu-ls&t=218s) A dip in mood gets blamed on the job
- [04:06](https://www.youtube.com/watch?v=7F2wctXu-ls&t=246s) Being a doctor as a safety net for entrepreneurship
- [05:10](https://www.youtube.com/watch?v=7F2wctXu-ls&t=310s) Sami's own leap at forty
- [05:32](https://www.youtube.com/watch?v=7F2wctXu-ls&t=332s) On-call duty taught workflow control
- [06:15](https://www.youtube.com/watch?v=7F2wctXu-ls&t=375s) An MBA alongside entrepreneurship — accounting is wonderful
- [07:06](https://www.youtube.com/watch?v=7F2wctXu-ls&t=426s) EMBA courses and the adult learner's edge
- [07:56](https://www.youtube.com/watch?v=7F2wctXu-ls&t=476s) Edtech as an investment target, and Spark VC
- [08:12](https://www.youtube.com/watch?v=7F2wctXu-ls&t=492s) Investment philosophy after the exit
- [09:36](https://www.youtube.com/watch?v=7F2wctXu-ls&t=576s) A sceptical temperament and set and forget
- [10:13](https://www.youtube.com/watch?v=7F2wctXu-ls&t=613s) Real estate and startups — the common denominator
- [10:49](https://www.youtube.com/watch?v=7F2wctXu-ls&t=649s) Care-property yield and the index as an alternative
- [11:13](https://www.youtube.com/watch?v=7F2wctXu-ls&t=673s) Lesson learned: the US at least at world weight
- [11:28](https://www.youtube.com/watch?v=7F2wctXu-ls&t=688s) FiBAN membership and the weight of a board seat
- [12:12](https://www.youtube.com/watch?v=7F2wctXu-ls&t=732s) Intensive support for the intellectually interesting
- [13:08](https://www.youtube.com/watch?v=7F2wctXu-ls&t=788s) B2B, software, analytics and language technologies
- [13:39](https://www.youtube.com/watch?v=7F2wctXu-ls&t=819s) Entrepreneur-to-entrepreneur support and hard pressure
- [14:35](https://www.youtube.com/watch?v=7F2wctXu-ls&t=875s) On call in Nivala: nobody says no to the boss
- [15:23](https://www.youtube.com/watch?v=7F2wctXu-ls&t=923s) The founder's bubble and loneliness
- [16:09](https://www.youtube.com/watch?v=7F2wctXu-ls&t=969s) Knowing how to ask for advice — is the problem the right one
- [16:34](https://www.youtube.com/watch?v=7F2wctXu-ls&t=994s) A 15k landing page versus a zero budget
- [17:02](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1022s) Experts only at the exit stage
- [17:12](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1032s) Secondary deals and expectations of the exit
- [18:04](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1084s) The culture of A, B and C rounds is changing
- [18:28](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1108s) A hundred grand in the account keeps the hunger up
- [18:43](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1123s) Founders do not grasp the end value
- [19:20](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1160s) Engeström's unicorn model versus 2x returns
- [20:09](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1209s) The angel investor's stochastics and surprise offers
- [21:07](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1267s) Down rounds and consistent valuation growth
- [21:45](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1305s) Cognitive dissonance for the earlier investors
- [22:00](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1320s) Look one round ahead
- [22:29](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1349s) The SaaS model: where scalability comes from
- [23:42](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1422s) The mathematical predictability of growth
- [24:19](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1459s) The aim of the A round and its illusion
- [25:01](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1501s) KPIs: gross margin, CAC and churn
- [25:58](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1558s) Zero churn is pure heroin
- [26:18](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1578s) Finland's few companies above five million ARR
- [26:37](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1597s) Midaxo moved to Boston and hired American sellers
- [27:03](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1623s) Kim Väisänen and the wrong kind of internationalisation
- [27:50](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1670s) A national of the country sells to nationals of that country
- [28:42](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1722s) The first office close by, physically and culturally
- [29:16](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1756s) Market size is not the bottleneck
- [29:30](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1770s) The founder goes to smell the gunpowder of the battlefield
- [29:53](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1793s) The first hire is make or break
- [30:16](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1816s) The price of internationalisation: 200 grand
- [30:56](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1856s) Complex B2B SaaS does not onboard itself
- [31:16](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1876s) Freemium works in games, not in B2B
- [31:36](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1896s) Manic play, one game at a time
- [32:26](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1946s) Apple's and China's manoeuvres
- [33:20](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2000s) WordDive, Duolingo and a critique of UI
- [34:14](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2054s) Finland's problem with usability design
- [35:10](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2110s) A UX improvement raises the price by 30 percent
- [35:55](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2155s) Inconsistency as a lack of competence
- [36:55](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2215s) How Finland gets more angels
- [37:48](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2268s) Angel investors are mostly amateurs
- [38:59](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2339s) A portfolio of 29 startups — only now am I learning
- [39:20](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2360s) You need a statistical base of 20 to 40 companies
- [40:16](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2416s) The Somali Warriors Slack community
- [40:56](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2456s) The entrepreneur's 125 percent load and the sermon service
- [41:38](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2498s) You reach founders only by investing
- [42:14](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2534s) Five daughters and four decades of sleep deprivation
- [42:34](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2554s) Eight-to-four success stories are rubbish
- [43:04](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2584s) The spread of working hours across the portfolio
- [44:53](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2693s) Burn the boats — the power of focus
- [45:06](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2706s) A small ticket and consistent development
- [45:32](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2732s) Ethics: to whom may illiquid assets be sold
- [46:44](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2804s) Closing vision: Helsinki as an international startup hub
- [48:01](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2881s) Call Sami first, then Ali

## Summary

Ali Omar, who began his career as a doctor and co-founded Med Group with Kustaa Piha, explains how a career change worked when medicine remained a fallback for the risk. The second half is about angel investing: why the portfolio leans on property and startups rather than listed equities, why a ten-to-fifteen-year leg demands patience, how SaaS metrics — gross margin, customer acquisition cost — drive the investment decision, and why the first overseas sales hire in an internationalising company costs more than anyone expects.

## Chapters

- [**00:00**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=0s) — Cold open: an intensive investor and B2B software
- [**00:29**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=29s) — Introducing Ali Omar
- [**00:44**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=44s) — From doctor to founder of Med Group
- [**01:12**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=72s) — Zero to a hundred million with Kustaa Piha
- [**01:41**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=101s) — A provocative LinkedIn post about changing careers
- [**02:23**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=143s) — Why career changers walk into the jaws of death
- [**02:44**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=164s) — Tacit knowledge and underrating your own competence
- [**03:38**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=218s) — A dip in mood gets blamed on the job
- [**04:06**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=246s) — Being a doctor as a safety net for entrepreneurship
- [**05:10**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=310s) — Sami's own leap at forty
- [**05:32**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=332s) — On-call duty taught workflow control
- [**06:15**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=375s) — An MBA alongside entrepreneurship — accounting is wonderful
- [**07:06**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=426s) — EMBA courses and the adult learner's edge
- [**07:56**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=476s) — Edtech as an investment target, and Spark VC
- [**08:12**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=492s) — Investment philosophy after the exit
- [**09:36**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=576s) — A sceptical temperament and set and forget
- [**10:13**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=613s) — Real estate and startups — the common denominator
- [**10:49**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=649s) — Care-property yield and the index as an alternative
- [**11:13**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=673s) — Lesson learned: the US at least at world weight
- [**11:28**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=688s) — FiBAN membership and the weight of a board seat
- [**12:12**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=732s) — Intensive support for the intellectually interesting
- [**13:08**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=788s) — B2B, software, analytics and language technologies
- [**13:39**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=819s) — Entrepreneur-to-entrepreneur support and hard pressure
- [**14:35**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=875s) — On call in Nivala: nobody says no to the boss
- [**15:23**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=923s) — The founder's bubble and loneliness
- [**16:09**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=969s) — Knowing how to ask for advice — is the problem the right one
- [**16:34**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=994s) — A 15k landing page versus a zero budget
- [**17:02**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1022s) — Experts only at the exit stage
- [**17:12**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1032s) — Secondary deals and expectations of the exit
- [**18:04**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1084s) — The culture of A, B and C rounds is changing
- [**18:28**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1108s) — A hundred grand in the account keeps the hunger up
- [**18:43**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1123s) — Founders do not grasp the end value
- [**19:20**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1160s) — Engeström's unicorn model versus 2x returns
- [**20:09**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1209s) — The angel investor's stochastics and surprise offers
- [**21:07**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1267s) — Down rounds and consistent valuation growth
- [**21:45**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1305s) — Cognitive dissonance for the earlier investors
- [**22:00**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1320s) — Look one round ahead
- [**22:29**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1349s) — The SaaS model: where scalability comes from
- [**23:42**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1422s) — The mathematical predictability of growth
- [**24:19**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1459s) — The aim of the A round and its illusion
- [**25:01**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1501s) — KPIs: gross margin, CAC and churn
- [**25:58**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1558s) — Zero churn is pure heroin
- [**26:18**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1578s) — Finland's few companies above five million ARR
- [**26:37**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1597s) — Midaxo moved to Boston and hired American sellers
- [**27:03**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1623s) — Kim Väisänen and the wrong kind of internationalisation
- [**27:50**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1670s) — A national of the country sells to nationals of that country
- [**28:42**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1722s) — The first office close by, physically and culturally
- [**29:16**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1756s) — Market size is not the bottleneck
- [**29:30**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1770s) — The founder goes to smell the gunpowder of the battlefield
- [**29:53**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1793s) — The first hire is make or break
- [**30:16**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1816s) — The price of internationalisation: 200 grand
- [**30:56**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1856s) — Complex B2B SaaS does not onboard itself
- [**31:16**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1876s) — Freemium works in games, not in B2B
- [**31:36**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1896s) — Manic play, one game at a time
- [**32:26**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=1946s) — Apple's and China's manoeuvres
- [**33:20**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2000s) — WordDive, Duolingo and a critique of UI
- [**34:14**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2054s) — Finland's problem with usability design
- [**35:10**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2110s) — A UX improvement raises the price by 30 percent
- [**35:55**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2155s) — Inconsistency as a lack of competence
- [**36:55**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2215s) — How Finland gets more angels
- [**37:48**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2268s) — Angel investors are mostly amateurs
- [**38:59**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2339s) — A portfolio of 29 startups — only now am I learning
- [**39:20**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2360s) — You need a statistical base of 20 to 40 companies
- [**40:16**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2416s) — The Somali Warriors Slack community
- [**40:56**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2456s) — The entrepreneur's 125 percent load and the sermon service
- [**41:38**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2498s) — You reach founders only by investing
- [**42:14**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2534s) — Five daughters and four decades of sleep deprivation
- [**42:34**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2554s) — Eight-to-four success stories are rubbish
- [**43:04**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2584s) — The spread of working hours across the portfolio
- [**44:53**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2693s) — Burn the boats — the power of focus
- [**45:06**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2706s) — A small ticket and consistent development
- [**45:32**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2732s) — Ethics: to whom may illiquid assets be sold
- [**46:44**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2804s) — Closing vision: Helsinki as an international startup hub
- [**48:01**](https://www.youtube.com/watch?v=7F2wctXu-ls&t=2881s) — Call Sami first, then Ali

## Watch

The recording lives on the Neuvottelija channel: [Uran vaihto Enkelisijoitukset | Omar | #neuvottelija 35](https://www.youtube.com/watch?v=7F2wctXu-ls).
A Finnish edition of this episode is published at [www.neuvottelija.fi](https://www.neuvottelija.fi/fi/episodes/41-uran-vaihto-enkelisijoitukset-omar-neuvottelija-35).

---

Cite as: Sami Miettinen, Neuvottelija — Career change and angel investing | Ali Omar | Negotiator 35, https://www.neuvottelija.com/podcast/episodes/ep35-uranvaihto-ja-enkelisijoittaminen-ali-omar/, 2020-09-04. For quotes include episode 35 and timestamp.